dataset_id large_stringclasses 414
values | reaction_id large_stringlengths 36 36 | reaction_smiles large_stringlengths 4 873 | rxn_insight_reaction large_stringlengths 19 1.07k | mapped_reaction_smiles large_stringlengths 14 3.37k | reactant_smiles large_stringlengths 1 581 | product_smiles large_stringlengths 1 433 | reagent_smiles large_stringclasses 634
values | catalyst_smiles large_stringlengths 1 683 ⌀ | solvent_smiles large_stringlengths 1 245 ⌀ | rxn_insight_class large_stringclasses 11
values | rxn_insight_name large_stringclasses 346
values | rxn_insight_tag large_stringlengths 64 64 | rxn_insight_tag2 large_stringlengths 64 64 | rxn_insight_scaffold large_stringlengths 5 288 ⌀ | rxn_insight_template large_stringlengths 24 2.64k ⌀ | yield_percent float64 -0.8 90,205,160,000B ⌀ | yield_measurements large_stringlengths 2 864 | temperature_value float64 -230 30.1k ⌀ | temperature_units large_stringclasses 3
values | reaction_time_value float64 0 4k ⌀ | time_units large_stringclasses 4
values | procedure_details large_stringlengths 1 23.6k ⌀ | reference large_stringclasses 96
values | doi large_stringclasses 19
values | functional_groups_reactants large_stringlengths 3 716 ⌀ | functional_groups_products large_stringlengths 3 539 ⌀ | participating_rings_reactants large_stringlengths 5 293 ⌀ | participating_rings_products large_stringlengths 5 271 ⌀ | all_rings_products large_stringlengths 5 271 ⌀ | byproduct_smiles large_stringclasses 176
values | agent_smiles large_stringlengths 1 712 ⌀ | temperature_c float64 -230 30.1k ⌀ | reaction_time_hours float64 0 2.16k ⌀ | reaction_smiles_with_agents large_stringlengths 4 882 |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-5b31adaad99b4385ac09b713c5c66eed | COc1cc(C(=O)NCCc2ccccc2)cc([N+](=O)[O-])c1OC>>COc1cc(C2=NCCc3ccccc32)cc([N+](=O)[O-])c1OC | COC=1C=C(C(=O)NCCC2=CC=CC=C2)C=C(C1OC)[N+](=O)[O-].P(=O)(Cl)(Cl)Cl>>COC=1C=C(C=C(C1OC)[N+](=O)[O-])C1=NCCC2=CC=CC=C12 | O=[C:6]([c:5]1[cH:4][c:3]([O:2][CH3:1])[c:21]([O:22][CH3:23])[c:17]([N+:18](=[O:19])[O-:20])[cH:16]1)[NH:7][CH2:8][CH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][cH:15]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6]2=[N:7][CH2:8][CH2:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]32)[cH:16][c:17]([N+:18](=[O:19])[O-:20])[c:21]1[O:22][CH... | COc1cc(C(=O)NCCc2ccccc2)cc([N+](=O)[O-])c1OC | COc1cc(C2=NCCc3ccccc32)cc([N+](=O)[O-])c1OC | null | null | null | Functional Group Interconversion | OtherReaction | 3d130227d6289b603b0e08a0df168cbdf5b579486c532fbe046c60faa6f7b086 | 9a0028c9231ad50183d9c88210ee9a64bc3340b25c296d3055a236dfcf8224cb | c1ccc(C2=NCCc3ccccc32)cc1 | O=[C;H0;D3;+0:1](-[NH;D2;+0:2]-[C:3]-[C:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9])-[c:10](:[c:11]):[c:12]>>[c:6]:[c:5]1:[c;H0;D3;+0:7](:[c:8]:[c:9])-[C;H0;D3;+0:1](-[c:10](:[c:11]):[c:12])=[N;H0;D2;+0:2]-[C:3]-[C:4]-1 | null | [] | null | null | null | null | 3.6 g of 3,4-dimethoxy-5-nitro-N-phenethylbenzamide are heated under reflux with 36 ml of phosphorus oxychloride under a nitrogen atmosphere for 96 hours. After distilling the excess phosphorus oxychloride in a water-jet vacuum at 60°, the residue is treated three times with 100 ml of toluene each time, with the solven... | 10.6084/m9.figshare.5104873.v1 | null | Secondary amide | Substituted imine | c1ccccc1 | C1=NCCc2ccccc21 | c1ccccc1.C1=NCCc2ccccc21 | HO- | null | null | null | COc1cc(C(=O)NCCc2ccccc2)cc([N+](=O)[O-])c1OC>>COc1cc(C2=NCCc3ccccc32)cc([N+](=O)[O-])c1OC |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-c321313ebc494c5cbbede5c4200ded16 | COc1cc(C2=NCCc3ccccc32)cc([N+](=O)[O-])c1OC>>O=[N+]([O-])c1cc(C2=NCCc3ccccc32)cc(O)c1O | COC=1C=C(C=C(C1OC)[N+](=O)[O-])C1=NCCC2=CC=CC=C12.Br>>Br.C1(=NCCC2=CC=CC=C12)C1=CC(=C(C(O)=C1)O)[N+](=O)[O-] | C[O:20][c:19]1[cH:18][c:7]([C:8]2=[N:9][CH2:10][CH2:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]32)[cH:6][c:5]([N+:3](=[O:2])[O-:4])[c:21]1[O:22]C>>[O:2]=[N+:3]([O-:4])[c:5]1[cH:6][c:7]([C:8]2=[N:9][CH2:10][CH2:11][c:12]3[cH:13][cH:14][cH:15][cH:16][c:17]32)[cH:18][c:19]([OH:20])[c:21]1[OH:22] | COc1cc(C2=NCCc3ccccc32)cc([N+](=O)[O-])c1OC | O=[N+]([O-])c1cc(C2=NCCc3ccccc32)cc(O)c1O | null | null | null | Deprotection | OtherReaction | a0f05885bbc65ae2846cad0ac34029941211b2ef3a426958b0c8aa83bb16fe86 | 9df751cd682ad9d54ed75d7313aaead6a019c5d37ede15c4672866d319b900ff | c1ccc(C2=NCCc3ccccc32)cc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4](-[O;H0;D2;+0:5]-C):[c:6]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4](-[OH;D1;+0:5]):[c:6] | null | [] | null | null | null | null | 1.4 g of 1-(3,4-dimethoxy-5-nitrophenyl)-3,4-dihydroisoquinoline are treated with 15 ml of constant-boiling hydrobromic acid and heated to boiling under reflux under a nitrogen atmosphere for 1.5 hours. After distilling the hydrobromic acid in a water-jet vacuum, the crystalline residue is recrystallized from acetone. ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aromatic alcohol.Aromatic alcohol | null | null | c1ccccc1.C1=NCCc2ccccc21 | Other | null | null | null | COc1cc(C2=NCCc3ccccc32)cc([N+](=O)[O-])c1OC>>O=[N+]([O-])c1cc(C2=NCCc3ccccc32)cc(O)c1O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-5756335bac1345b98f6e307f0bc24576 | COc1cc(C=O)cc(C=O)c1O>>O=Cc1cc(O)c(O)c(C=O)c1 | OC1=C(C=C(C=O)C=C1OC)C=O.Br>>OC1=C(C=C(C=O)C=C1O)C=O | C[O:6][c:5]1[cH:4][c:3]([CH:2]=[O:1])[cH:12][c:9]([CH:10]=[O:11])[c:7]1[OH:8]>>[O:1]=[CH:2][c:3]1[cH:4][c:5]([OH:6])[c:7]([OH:8])[c:9]([CH:10]=[O:11])[cH:12]1 | COc1cc(C=O)cc(C=O)c1O | O=Cc1cc(O)c(O)c(C=O)c1 | null | null | null | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccccc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 3 | HOUR | 5.0 g of 4-hydroxy-5-methoxy-isophthalaldehyde are treated with 50 ml of constant-boiling hydrobromic acid and heated to boiling under reflux and while stirring under an argon atmosphere for 3 hours. After cooling 50 ml of ice-water are added thereto, and the separated precipitate is filtered under suction and washed w... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1 | Other | null | null | 3 | COc1cc(C=O)cc(C=O)c1O>>O=Cc1cc(O)c(O)c(C=O)c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-30f6d43a188b4882abf7f89bd21c9ed9 | COc1cc(C(=O)CBr)ccc1O.O=[N+]([O-])O>>COc1cc(C(=O)CBr)cc([N+](=O)[O-])c1O | [N+](=O)(O)[O-].BrCC(=O)C1=CC(=C(C=C1)O)OC>>BrCC(=O)C1=CC(=C(C(=C1)[N+](=O)[O-])O)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[CH2:8][Br:9])[cH:10][cH:11][c:15]1[OH:16].O[N+:12](=[O:13])[O-:14]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[CH2:8][Br:9])[cH:10][c:11]([N+:12](=[O:13])[O-:14])[c:15]1[OH:16] | COc1cc(C(=O)CBr)ccc1O.O=[N+]([O-])O | COc1cc(C(=O)CBr)cc([N+](=O)[O-])c1O | null | null | C(C)(=O)O | Functional Group Addition | Aromatic nitration with HNO3 | 53848b8b2bb4e867226e49db2e60519b24be9379900e3ad7c56af54fe8fde7a5 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | c1ccccc1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[O;D1;H0:4]=[C:5]-[c:6]:[c:7]:[cH;D2;+0:8]:[c:9](-[O;D1;H1:10]):[c:11]>>[O;-;D1;H0:2]-[N+;H0;D3:1](=[O;D1;H0:3])-[c;H0;D3;+0:8](:[c:7]:[c:6]-[C:5]=[O;D1;H0:4]):[c:9](-[O;D1;H1:10]):[c:11] | null | [] | null | null | null | null | A solution of 38 g of fuming nitric acid (96%) in 50 ml of glacial acetic acid is added dropwise while stirring and within 30 minutes at 20°-25° to a solution of 112.5 g of 2-bromo-4'-hydroxy-3'-methoxyacetophenone in 560 ml of glacial acetic acid. Yellow-brown crystals thereby separate. After 90 minutes the reaction m... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | C(C)(=O)O | null | null | COc1cc(C(=O)CBr)ccc1O.O=[N+]([O-])O>C(C)(=O)O>COc1cc(C(=O)CBr)cc([N+](=O)[O-])c1O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-657381fee6594bcc800e24778971091f | CCO.COc1cc(C(=O)CBr)cc([N+](=O)[O-])c1O>>CCOC(=O)C(=O)c1cc(OC)c(O)c([N+](=O)[O-])c1 | BrCC(=O)C1=CC(=C(C(=C1)[N+](=O)[O-])O)OC.C(C)O.[Se](=O)=O>>OC1=C(C=C(C=C1[N+](=O)[O-])C(C(=O)OCC)=O)OC | [CH3:1][CH2:2][OH:3].Br[CH2:4][C:6](=[O:7])[c:8]1[cH:9][c:10]([O:11][CH3:12])[c:13]([OH:14])[c:15]([N+:16](=[O:17])[O-:18])[cH:19]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[O:7])[c:8]1[cH:9][c:10]([O:11][CH3:12])[c:13]([OH:14])[c:15]([N+:16](=[O:17])[O-:18])[cH:19]1 | CCO.COc1cc(C(=O)CBr)cc([N+](=O)[O-])c1O | CCOC(=O)C(=O)c1cc(OC)c(O)c([N+](=O)[O-])c1 | null | null | null | Acylation | OtherReaction | fd2eb18b6571f5871d34af3ee3047ac4a3cf01c29ff7067109d016d3324c22a1 | 6a9d9df581b58124b36acc38fbe3ba14c5c991095298763ede7bc1de3bebb9ed | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[C;D1;H3:5]-[C:6]-[OH;D1;+0:7]>>[C;D1;H3:5]-[C:6]-[O;H0;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:8])-[C:2](=[O;D1;H0:3])-[c:4] | null | [] | null | null | null | null | ba) A suspension of 580.1 mg of 2-bromo-4'-hydroxy-3'-methoxy-5'-nitroacetophenone in 10 ml of ethanol is treated with 443.8 mg of selenium dioxide and heated under reflux for 71 hours. Thereafter, the selenium is removed by filtration and the filtrate is evaporated. The residue is dissolved in methylene chloride, wash... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Primary alcohol | Ketone.Ester | null | null | c1ccccc1 | null | null | null | null | CCO.COc1cc(C(=O)CBr)cc([N+](=O)[O-])c1O>>CCOC(=O)C(=O)c1cc(OC)c(O)c([N+](=O)[O-])c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-06921af03d4d48e7a343702b914bbf0e | CO.COc1cc(C(=O)C(=O)O)cc([N+](=O)[O-])c1O>>COC(=O)C(=O)c1cc(OC)c(O)c([N+](=O)[O-])c1 | CO.OC1=C(C=C(C=C1[N+](=O)[O-])C(C(=O)O)=O)OC>>OC1=C(C=C(C=C1[N+](=O)[O-])C(C(=O)OC)=O)OC | [CH3:1][OH:2].O[C:3](=[O:4])[C:5](=[O:6])[c:7]1[cH:8][c:9]([O:10][CH3:11])[c:12]([OH:13])[c:14]([N+:15](=[O:16])[O-:17])[cH:18]1>>[CH3:1][O:2][C:3](=[O:4])[C:5](=[O:6])[c:7]1[cH:8][c:9]([O:10][CH3:11])[c:12]([OH:13])[c:14]([N+:15](=[O:16])[O-:17])[cH:18]1 | CO.COc1cc(C(=O)C(=O)O)cc([N+](=O)[O-])c1O | COC(=O)C(=O)c1cc(OC)c(O)c([N+](=O)[O-])c1 | null | CN(C1=CC=NC=C1)C | CN(C=O)C | Protection | Esterification of Carboxylic Acids | 39d16bd3d272c159d0b6bdffdfc1604638f8bf4a0e031197ec1b2e8908685cf8 | 231ff3c26ec4913351b94dfe764f541c276067efdaca386b0caa3c39256d1ff1 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](=[O;D1;H0:4])-[c:5].[C;D1;H3:6]-[OH;D1;+0:7]>>[C;D1;H3:6]-[O;H0;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](=[O;D1;H0:4])-[c:5] | null | [] | null | null | 1 | HOUR | 2.42 g of 4-hydroxy-3-methoxy-5-nitrophenylglyoxylic acid are dissolved in 25 ml of dry N,N-dimethylformamide, treated at room temperature with 50 mg of 4-dimethylaminopyridine and 920 mg of dry methanol, subsequently cooled to 0° with an ice-bath and 2.27 g of N,N-dicyclohexylcarbodiimide are added thereto. After 10 m... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Ketone.Methanol | Ketone.Ester | null | null | c1ccccc1 | HO- | CN(C1=CC=NC=C1)C.CN(C=O)C | null | 1 | CO.COc1cc(C(=O)C(=O)O)cc([N+](=O)[O-])c1O>CN(C1=CC=NC=C1)C.CN(C=O)C>COC(=O)C(=O)c1cc(OC)c(O)c([N+](=O)[O-])c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-cf8e84553e394b2c88969c0f931250e1 | CCOC(=O)C(=O)c1cc(OC)c(O)c([N+](=O)[O-])c1>>CCOC(=O)C(=O)c1cc(O)c(O)c([N+](=O)[O-])c1 | OC1=C(C=C(C=C1[N+](=O)[O-])C(C(=O)OCC)=O)OC.[I-].[Na+].[Si](Cl)(Cl)(Cl)Cl>>OC=1C=C(C=C(C1O)[N+](=O)[O-])C(C(=O)OCC)=O | C[O:11][c:10]1[cH:9][c:8]([C:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])=[O:7])[cH:18][c:14]([N+:15](=[O:16])[O-:17])[c:12]1[OH:13]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[C:6](=[O:7])[c:8]1[cH:9][c:10]([OH:11])[c:12]([OH:13])[c:14]([N+:15](=[O:16])[O-:17])[cH:18]1 | CCOC(=O)C(=O)c1cc(OC)c(O)c([N+](=O)[O-])c1 | CCOC(=O)C(=O)c1cc(O)c(O)c([N+](=O)[O-])c1 | null | null | C(C)#N.C1(=CC=CC=C1)C | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccccc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | A suspension of 17.2 g of ethyl 4-hydroxy-3-methoxy-5-nitrophenylglyoxylate in 100 ml of dry acetonitrile and 100 ml of dry toluene is treated with 10.53 g of sodium iodide and 11.9 g of silicon tetrachloride and heated under reflux for 47 hours. The reaction mixture is then evaporated and the residue is distilled six ... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1 | Other | C(C)#N.C1(=CC=CC=C1)C | null | null | CCOC(=O)C(=O)c1cc(OC)c(O)c([N+](=O)[O-])c1>C(C)#N.C1(=CC=CC=C1)C>CCOC(=O)C(=O)c1cc(O)c(O)c([N+](=O)[O-])c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-29694de871a1417693a0aa82e55132f8 | CCCCCCOC(=O)C(=O)c1cc(O)c(O)c([N+](=O)[O-])c1.Nc1ccccc1O>>O=c1oc2ccccc2nc1-c1cc(O)c(O)c([N+](=O)[O-])c1 | OC=1C=C(C=C(C1O)[N+](=O)[O-])C(C(=O)OCCCCCC)=O.NC1=C(C=CC=C1)O>>OC=1C=C(C=C(C1O)[N+](=O)[O-])C=1C(OC2=C(N1)C=CC=C2)=O | CCCCCCO[C:2](=[O:1])[C:11](=O)[c:12]1[cH:13][c:14]([OH:15])[c:16]([OH:17])[c:18]([N+:19](=[O:20])[O-:21])[cH:22]1.[OH:3][c:4]1[cH:5][cH:6][cH:7][cH:8][c:9]1[NH2:10]>>[O:1]=[c:2]1[o:3][c:4]2[cH:5][cH:6][cH:7][cH:8][c:9]2[n:10][c:11]1-[c:12]1[cH:13][c:14]([OH:15])[c:16]([OH:17])[c:18]([N+:19](=[O:20])[O-:21])[cH:22]1 | CCCCCCOC(=O)C(=O)c1cc(O)c(O)c([N+](=O)[O-])c1.Nc1ccccc1O | O=c1oc2ccccc2nc1-c1cc(O)c(O)c([N+](=O)[O-])c1 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 5e1d673dfabaa960b39ee552387c6ad36e84700fab0cedc505bddfd866b66602 | c7371540e6bbfa0cc65c0d222916a85bfb12611676b69973853bf515c0385853 | O=c1oc2ccccc2nc1-c1ccccc1 | C-C-C-C-C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3](=O)-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12](-[OH;D1;+0:13]):[c:14]>>[O;D1;H0:2]=[c;H0;D3;+0:1]1:[o;H0;D2;+0:13]:[c:12](:[c:14]):[c:10](:[c:11]):[n;H0;D2;+0:9]:[c;H0;D3;+0:3]:1-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8] | null | [] | null | null | null | null | A mixture of 3.93 g of n-hexyl 3,4-dihydroxy-5-nitrophenylglyoxylate and 1.38 g of 2-aminophenol is melted at 120° while stirring. The melt crystallizes after 5 minutes. After 2 hours it is cooled and recrystallized from methanol. There is obtained 3-(3,4-dihydroxy-5-nitrophenyl)-2H-1,4-benzoxazin-2-one of m.p. 202°-20... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Aromatic alcohol.Primary amine | null | c1ccccc1 | c1coc2ccccc2n1 | c1coc2ccccc2n1.c1ccccc1 | HO- | null | null | null | CCCCCCOC(=O)C(=O)c1cc(O)c(O)c([N+](=O)[O-])c1.Nc1ccccc1O>>O=c1oc2ccccc2nc1-c1cc(O)c(O)c([N+](=O)[O-])c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-445b7c4eb9bb4662a89b322d78b7d270 | CCCCCCOC(=O)C(=O)c1cc(O)c(O)c([N+](=O)[O-])c1.Nc1cc2ccccc2cc1N>>O=c1[nH]c2cc3ccccc3cc2nc1-c1cc(O)c(O)c([N+](=O)[O-])c1 | OC=1C=C(C=C(C1O)[N+](=O)[O-])C(C(=O)OCCCCCC)=O.NC1=CC2=CC=CC=C2C=C1N>>OC=1C=C(C=C(C1O)[N+](=O)[O-])C1=NC=2C=C3C(=CC2NC1=O)C=CC=C3 | CCCCCCO[C:2](=[O:1])[C:15](=O)[c:16]1[cH:17][c:18]([OH:19])[c:20]([OH:21])[c:22]([N+:23](=[O:24])[O-:25])[cH:26]1.[NH2:3][c:4]1[cH:5][c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[cH:12][c:13]1[NH2:14]>>[O:1]=[c:2]1[nH:3][c:4]2[cH:5][c:6]3[cH:7][cH:8][cH:9][cH:10][c:11]3[cH:12][c:13]2[n:14][c:15]1-[c:16]1[cH:17][c:18]([OH:19])... | CCCCCCOC(=O)C(=O)c1cc(O)c(O)c([N+](=O)[O-])c1.Nc1cc2ccccc2cc1N | O=c1[nH]c2cc3ccccc3cc2nc1-c1cc(O)c(O)c([N+](=O)[O-])c1 | null | null | CO.C(CCCCC)O | Aromatic Heterocycle Formation | OtherReaction | 932e27837b2ecefcb66bf6339e54a584f6875cd8fc746a7aa5b03150b570b7f8 | e28c800b2735165056723890e12c2ad9c1d2da47ee7ccbf1f368d59707889e86 | O=c1[nH]c2cc3ccccc3cc2nc1-c1ccccc1 | C-C-C-C-C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3](=O)-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12](-[NH2;D1;+0:13]):[c:14]>>[O;D1;H0:2]=[c;H0;D3;+0:1]1:[nH;D2;+0:13]:[c:12](:[c:14]):[c:10](:[c:11]):[n;H0;D2;+0:9]:[c;H0;D3;+0:3]:1-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8] | null | [] | null | null | null | null | A solution of 1.07 g of n-hexyl 3,4-dihydroxy-5-nitrophenylglyoxylate and 696.3 mg of 2,3-diaminonaphthalene in 3 ml of 1-hexanol is heated to boiling under reflux for 3 hours. The reaction mixture is then cooled and diluted with methanol. The crude product is filtered under suction and recrystallized from N,N-dimethyl... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Primary amine.Primary amine | null | c1ccc2ccccc2c1 | c1cnc2cc3ccccc3cc2n1 | c1cnc2cc3ccccc3cc2n1.c1ccccc1 | HO- | CO.C(CCCCC)O | null | null | CCCCCCOC(=O)C(=O)c1cc(O)c(O)c([N+](=O)[O-])c1.Nc1cc2ccccc2cc1N>CO.C(CCCCC)O>O=c1[nH]c2cc3ccccc3cc2nc1-c1cc(O)c(O)c([N+](=O)[O-])c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-3dd1f8d05a064ef297861381ff86be83 | CCCCCCOC(=O)C(=O)c1cc(O)c(O)c([N+](=O)[O-])c1.NNC(N)=S>>O=c1[nH]c(S)nnc1-c1cc(O)c(O)c([N+](=O)[O-])c1 | Cl.[OH-].[Na+].OC=1C=C(C=C(C1O)[N+](=O)[O-])C(C(=O)OCCCCCC)=O.NNC(=S)N>>OC=1C=C(C=C(C1O)[N+](=O)[O-])C=1C(NC(=NN1)S)=O | CCCCCCO[C:2](=[O:1])[C:8](=O)[c:9]1[cH:10][c:11]([OH:12])[c:13]([OH:14])[c:15]([N+:16](=[O:17])[O-:18])[cH:19]1.[NH2:3][C:4](=[S:5])[NH:6][NH2:7]>>[O:1]=[c:2]1[nH:3][c:4]([SH:5])[n:6][n:7][c:8]1-[c:9]1[cH:10][c:11]([OH:12])[c:13]([OH:14])[c:15]([N+:16](=[O:17])[O-:18])[cH:19]1 | CCCCCCOC(=O)C(=O)c1cc(O)c(O)c([N+](=O)[O-])c1.NNC(N)=S | O=c1[nH]c(S)nnc1-c1cc(O)c(O)c([N+](=O)[O-])c1 | null | null | O | Aromatic Heterocycle Formation | OtherReaction | d7b2654a575aa9f209d74f5f390458815c6178e6906a1d6c685dc175a199aa86 | 2f2fdbba936ef8ea71e21796aff8dc80081c6ffc70053b005dc6154b8db4c97f | O=c1[nH]cnnc1-c1ccccc1 | C-C-C-C-C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3](=O)-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8].[NH2;D1;+0:9]-[C;H0;D3;+0:10](=[S;H0;D1;+0:11])-[NH;D2;+0:12]-[NH2;D1;+0:13]>>[O;D1;H0:2]=[c;H0;D3;+0:1]1:[nH;D2;+0:9]:[c;H0;D3;+0:10](-[SH;D1;+0:11]):[n;H0;D2;+0:12]:[n;H0;D2;+0:13]:[c;H0;D3;+0:3]:1-[c;H0;D3;+0:4](:[... | null | [] | null | null | 30 | MINUTE | A suspension of 2.05 g of n-hexyl 3,4-dihydroxy-5-nitrophenylglyoxylate and 600.8 mg of thiosemicarbazide is stirred intensively at 90° for 30 minutes. The mixture is then cooled to 40° and treated with a solution of 870.1 mg of sodium hydroxide in 15 ml of water. The solution is subsequently heated to 90° for 30 minut... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Ester.Thiourea | Aromatic thiol | null | c1cnncn1 | c1cnncn1.c1ccccc1 | HO- | O | null | 0.5 | CCCCCCOC(=O)C(=O)c1cc(O)c(O)c([N+](=O)[O-])c1.NNC(N)=S>O>O=c1[nH]c(S)nnc1-c1cc(O)c(O)c([N+](=O)[O-])c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-70beeb816f21435f979acae0bf102bab | COc1cc(C(=O)CBr)cc([N+](=O)[O-])c1O.NC(N)=S>>COc1cc(-c2csc(N)n2)cc([N+](=O)[O-])c1O | BrCC(=O)C1=CC(=C(C(=C1)[N+](=O)[O-])O)OC.NC(=S)N.C(C)(=O)[O-].[Na+]>>NC=1SC=C(N1)C1=CC(=C(C(=C1)[N+](=O)[O-])O)OC | O=[C:6]([c:5]1[cH:4][c:3]([O:2][CH3:1])[c:17]([OH:18])[c:13]([N+:14](=[O:15])[O-:16])[cH:12]1)[CH2:7]Br.[S:8]=[C:9]([NH2:10])[NH2:11]>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][s:8][c:9]([NH2:10])[n:11]2)[cH:12][c:13]([N+:14](=[O:15])[O-:16])[c:17]1[OH:18] | COc1cc(C(=O)CBr)cc([N+](=O)[O-])c1O.NC(N)=S | COc1cc(-c2csc(N)n2)cc([N+](=O)[O-])c1O | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | bef473efef1d9ea696235ac9e0e73338149dac4bc5d824d8ecb15263a8e3a4b0 | 39fbe568f79251ca2d63e869c3b1ee705fef7458c6d99863e8f91d4da02df595 | c1ccc(-c2cscn2)cc1 | Br-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7].[N;D1;H2:8]-[C;H0;D3;+0:9](-[NH2;D1;+0:10])=[S;H0;D1;+0:11]>>[N;D1;H2:8]-[c;H0;D3;+0:9]1:[n;H0;D2;+0:10]:[c;H0;D3;+0:2](-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7]):[cH;D2;+0:1]:[s;H0;D2;+0:11]:1 | null | [] | null | null | 6 | HOUR | aaa) A suspension of 2.9 g of 2-bromo-4'-hydroxy-3'-methoxy-5'-nitroacetophenone and 761.2 mg of thiourea in 170 ml of ethanol is treated at 60° with 820.3 mg of sodium acetate and stirred for 6 hours. The reaction mixture is then evaporated, the residue is treated with 170 ml of water and heated to 60° for 30 minutes.... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Thiourea | null | null | c1cscn1 | c1ccccc1.c1cscn1 | HBr | C(C)O | null | 6 | COc1cc(C(=O)CBr)cc([N+](=O)[O-])c1O.NC(N)=S>C(C)O>COc1cc(-c2csc(N)n2)cc([N+](=O)[O-])c1O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-03b7bd662d1a4889abc766e94fc0d239 | COc1cc(C(=O)CBr)cc([N+](=O)[O-])c1O.NCC(=O)c1ccccc1>>COc1cc(C(=O)c2[nH]c3ccccc3c2C)cc([N+](=O)[O-])c1O | BrCC(=O)C1=CC(=C(C(=C1)[N+](=O)[O-])O)OC.NCC(=O)C1=CC=CC=C1.CN(C=O)C>>OC1=C(C=C(C(=O)C=2NC3=CC=CC=C3C2C)C=C1[N+](=O)[O-])OC | Br[CH2:8][C:6]([c:5]1[cH:4][c:3]([O:2][CH3:1])[c:23]([OH:24])[c:19]([N+:20](=[O:21])[O-:22])[cH:18]1)=[O:7].O=[C:16]([c:15]1[cH:10][cH:11][cH:12][cH:13][cH:14]1)[CH2:17][NH2:9]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[c:8]2[nH:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[c:16]2[CH3:17])[cH:18][c:19]([N+:20](=[O:21]... | COc1cc(C(=O)CBr)cc([N+](=O)[O-])c1O.NCC(=O)c1ccccc1 | COc1cc(C(=O)c2[nH]c3ccccc3c2C)cc([N+](=O)[O-])c1O | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 7501a2075c131a5a697be83b8893b35998b6f93f2cc7dbe47176bf49df74cf51 | 56ed520f4f13c3550ff850cebe88b7872ea827a3d10cfa555c019deb4ba80564 | O=C(c1ccccc1)c1cc2ccccc2[nH]1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].O=[C;H0;D3;+0:5](-[CH2;D2;+0:6]-[NH2;D1;+0:7])-[c:8](:[c:9]):[cH;D2;+0:10]:[c:11]:[c:12]>>[CH3;D1;+0:6]-[c;H0;D3;+0:5]1:[c:8](:[c:9]):[c;H0;D3;+0:10](:[c:11]:[c:12]):[nH;D2;+0:7]:[c;H0;D3;+0:1]:1-[C:2](=[O;D1;H0:3])-[c:4] | null | [] | null | null | null | null | ac) A solution of 29.0 g of 2-bromo-4'-hydroxy-3'-methoxy-5'-nitroacetophenone and 13.5 g of 2-aminoacetophenone in 250 ml of dry N,N-dimethylformamide is stirred at 90° for 16 hours. The reaction mixture is then evaporated to about two thirds and poured on to ice. The separated crystals are filtered under suction and ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Ketone.Primary amine | Ketone | c1ccccc1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1 | HBr | null | null | null | COc1cc(C(=O)CBr)cc([N+](=O)[O-])c1O.NCC(=O)c1ccccc1>>COc1cc(C(=O)c2[nH]c3ccccc3c2C)cc([N+](=O)[O-])c1O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-c1da424a960142718e6a9c76386cbb7d | COc1cc(C(=O)CBr)cc([N+](=O)[O-])c1O.Nc1ccccc1N>>COc1cc(-c2cnc3ccccc3n2)cc([N+](=O)[O-])c1O | BrCC(=O)C1=CC(=C(C(=C1)[N+](=O)[O-])O)OC.C1(=C(C=CC=C1)N)N.C(C)(=O)[O-].[Na+]>>OC1=C(C=C(C=C1[N+](=O)[O-])C1=NC2=CC=CC=C2N=C1)OC | O=[C:6]([c:5]1[cH:4][c:3]([O:2][CH3:1])[c:21]([OH:22])[c:17]([N+:18](=[O:19])[O-:20])[cH:16]1)[CH2:7]Br.[NH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[NH2:15]>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][n:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[n:15]2)[cH:16][c:17]([N+:18](=[O:19])[O-:20])[c:21]1[OH:22] | COc1cc(C(=O)CBr)cc([N+](=O)[O-])c1O.Nc1ccccc1N | COc1cc(-c2cnc3ccccc3n2)cc([N+](=O)[O-])c1O | null | null | CO | Aromatic Heterocycle Formation | OtherReaction | 90078f432f905ed0b4724dc219c64e2a45c6721a4693e9eb19593572b552eba8 | 9d47518c57b63d84db17ba0d9c072abf94bbc6e32abcdc7fc6190cbcdbd5c583 | c1ccc(-c2cnc3ccccc3n2)cc1 | Br-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[c:11](-[NH2;D1;+0:12]):[c:13]>>[c:13]:[c:11]1:[n;H0;D2;+0:12]:[cH;D2;+0:1]:[c;H0;D3;+0:2](-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7]):[n;H0;D2;+0:8]:[c:9]:1:[c:10] | null | [] | null | null | null | null | ada) A suspension of 14.5 g of 2-bromo-4'-hydroxy-3'-methoxy-5'-nitroacetophenone and 5.41 g of 1,2-phenylenediamine in 350 ml of methanol is treated with 4.92 g of sodium acetate and the mixture is heated to boiling under reflux for 22 hours. The reaction mixture is then evaporated, the residue is dissolved in methyle... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Primary amine.Primary amine | null | c1ccccc1 | c1ccc2nccnc2c1 | c1ccccc1.c1ccc2nccnc2c1 | HBr | CO | null | null | COc1cc(C(=O)CBr)cc([N+](=O)[O-])c1O.Nc1ccccc1N>CO>COc1cc(-c2cnc3ccccc3n2)cc([N+](=O)[O-])c1O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-7082e011baac43e2a5643bc71542a913 | BrB(Br)Br.COc1cc(-c2csc(N)n2)cc([N+](=O)[O-])c1O>>Br.Nc1nc(-c2cc(O)c(O)c([N+](=O)[O-])c2)cs1 | NC=1SC=C(N1)C1=CC(=C(C(=C1)[N+](=O)[O-])O)OC.B(Br)(Br)Br>>Br.NC=1SC=C(N1)C1=CC(=C(C(O)=C1)O)[N+](=O)[O-] | BrB(Br)[Br:1].C[O:9][c:8]1[cH:7][c:6](-[c:5]2[n:4][c:3]([NH2:2])[s:18][cH:17]2)[cH:16][c:12]([N+:13](=[O:14])[O-:15])[c:10]1[OH:11]>>[BrH:1].[NH2:2][c:3]1[n:4][c:5](-[c:6]2[cH:7][c:8]([OH:9])[c:10]([OH:11])[c:12]([N+:13](=[O:14])[O-:15])[cH:16]2)[cH:17][s:18]1 | BrB(Br)Br.COc1cc(-c2csc(N)n2)cc([N+](=O)[O-])c1O | Br.Nc1nc(-c2cc(O)c(O)c([N+](=O)[O-])c2)cs1 | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | 005318874c4792a3ed14897fb19099f1f6e548b285f476e19a15213a92356c2d | 0bab01685da92cdead9c84b3a9c513c0e9bd4114585991beae2460d8c47b3623 | c1ccc(-c2cscn2)cc1 | Br-B(-Br)-[Br;H0;D1;+0:1].C-[O;H0;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[BrH;D0;+0:1].[OH;D1;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | 1 | HOUR | A suspension of 267.3 mg of 4-(2-amino-4-thiazolyl)-2-methoxy-6-nitrophenol in 10 ml of dry methylene chloride is treated at -20° with 1.25 g of boron tribromide. After the addition the mixture is stirred at -20° for a further 1 hour and at room temperature without cooling for 18 hours. The reaction mixture is then eva... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1cscn1.c1ccccc1 | HBr.B | C(Cl)Cl | null | 1 | BrB(Br)Br.COc1cc(-c2csc(N)n2)cc([N+](=O)[O-])c1O>C(Cl)Cl>Br.Nc1nc(-c2cc(O)c(O)c([N+](=O)[O-])c2)cs1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-725b5ba5814b48eb98ba77b354505416 | CC(N)=S.O=C(CBr)c1cc(O)c(O)c([N+](=O)[O-])c1>>Br.Cc1nc(-c2cc(O)c(O)c([N+](=O)[O-])c2)cs1 | BrCC(=O)C1=CC(=C(C(=C1)[N+](=O)[O-])O)O.C(C)(=S)N>>Br.CC=1SC=C(N1)C1=CC(=C(C(O)=C1)O)[N+](=O)[O-] | [CH3:2][C:3]([NH2:4])=[S:18].O=[C:5]([c:6]1[cH:7][c:8]([OH:9])[c:10]([OH:11])[c:12]([N+:13](=[O:14])[O-:15])[cH:16]1)[CH2:17][Br:1]>>[BrH:1].[CH3:2][c:3]1[n:4][c:5](-[c:6]2[cH:7][c:8]([OH:9])[c:10]([OH:11])[c:12]([N+:13](=[O:14])[O-:15])[cH:16]2)[cH:17][s:18]1 | CC(N)=S.O=C(CBr)c1cc(O)c(O)c([N+](=O)[O-])c1 | Br.Cc1nc(-c2cc(O)c(O)c([N+](=O)[O-])c2)cs1 | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 21eb8c7cda3c7fc14309a0c556334226f1a9147c334386d33bc70341830a82ec | 9f145257a80f08f1a7a6ee36c84cd4115965bd63128f36de61c7ed688ad2603c | c1ccc(-c2cscn2)cc1 | O=[C;H0;D3;+0:1](-[CH2;D2;+0:2]-[Br;H0;D1;+0:3])-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8].[C;D1;H3:9]-[C;H0;D3;+0:10](-[NH2;D1;+0:11])=[S;H0;D1;+0:12]>>[BrH;D0;+0:3].[C;D1;H3:9]-[c;H0;D3;+0:10]1:[n;H0;D2;+0:11]:[c;H0;D3;+0:1](-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8]):[cH;D2;+0:2]:[s;H0;D2;+0:12]:1 | null | [] | null | null | null | null | A mixture of 3.12 g of 2-bromo-3',4'-dihydroxy-5'-nitroacetophenone and 849.3 mg of thioacetamide are heated to boiling under reflux for 18 hours in 40 ml of ethanol. After cooling, the crystals are filtered under suction and recrystallized from methanol/isopropanol. There is obtained 5-(2-methyl-4-thiazolyl)-3-nitropy... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Thioamide | null | null | c1cscn1 | c1cscn1.c1ccccc1 | HO- | C(C)O | null | null | CC(N)=S.O=C(CBr)c1cc(O)c(O)c([N+](=O)[O-])c1>C(C)O>Br.Cc1nc(-c2cc(O)c(O)c([N+](=O)[O-])c2)cs1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-cbbcb8695b35407abcb11ac2b06862cc | NNC(N)=S.O=C(CBr)c1cc(O)c(O)c([N+](=O)[O-])c1>>Br.NC1=NN=C(c2cc(O)c(O)c([N+](=O)[O-])c2)CS1 | BrCC(=O)C1=CC(=C(C(=C1)[N+](=O)[O-])O)O.NNC(=S)N>>Br.NC=1SCC(=NN1)C1=CC(=C(C(O)=C1)O)[N+](=O)[O-] | [NH2:2][C:3]([NH:4][NH2:5])=[S:19].O=[C:6]([c:7]1[cH:8][c:9]([OH:10])[c:11]([OH:12])[c:13]([N+:14](=[O:15])[O-:16])[cH:17]1)[CH2:18][Br:1]>>[BrH:1].[NH2:2][C:3]1=[N:4][N:5]=[C:6]([c:7]2[cH:8][c:9]([OH:10])[c:11]([OH:12])[c:13]([N+:14](=[O:15])[O-:16])[cH:17]2)[CH2:18][S:19]1 | NNC(N)=S.O=C(CBr)c1cc(O)c(O)c([N+](=O)[O-])c1 | Br.NC1=NN=C(c2cc(O)c(O)c([N+](=O)[O-])c2)CS1 | null | null | C(CCC)O | Functional Group Addition | OtherReaction | fd4918177f4108faf168d39dcea39a45556594e5deca0327428c99743a7b61de | 94553d397535d3f0cbd64ccf751c47533b97c42c61075b7687ef747351ab4987 | C1=NN=C(c2ccccc2)CS1 | O=[C;H0;D3;+0:1](-[CH2;D2;+0:2]-[Br;H0;D1;+0:3])-[c:4](:[c:5]):[c:6].[N;D1;H2:7]-[C;H0;D3;+0:8](=[S;H0;D1;+0:9])-[NH;D2;+0:10]-[NH2;D1;+0:11]>>[BrH;D0;+0:3].[N;D1;H2:7]-[C;H0;D3;+0:8]1=[N;H0;D2;+0:10]-[N;H0;D2;+0:11]=[C;H0;D3;+0:1](-[c:4](:[c:5]):[c:6])-[CH2;D2;+0:2]-[S;H0;D2;+0:9]-1 | null | [] | null | null | null | null | A solution of 1.38 g of 2-bromo-3',4'-dihydroxy-5'-nitroacetophenone and 461 mg of thiosemicarbazide in 20 ml of n-butanol is heated to boiling under reflux for 60 minutes. After cooling to room temperature the crystals are filtered under suction and recrystallized from n-butanol. There is obtained 5-(2-amino-6H-1,3,4-... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Primary halide.Ketone.Thiourea | Monosulfide | null | C1=NN=CSC1 | C1=NN=CSC1.c1ccccc1 | HO- | C(CCC)O | null | null | NNC(N)=S.O=C(CBr)c1cc(O)c(O)c([N+](=O)[O-])c1>C(CCC)O>Br.NC1=NN=C(c2cc(O)c(O)c([N+](=O)[O-])c2)CS1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ba0229b7adf84c588e3a45841bc2fd4e | Nc1nncs1.O=C(CBr)c1cc(O)c(O)c([N+](=O)[O-])c1>>O=[N+]([O-])c1cc(-c2cn3ncsc3n2)cc(O)c1O | BrCC(=O)C1=CC(=C(C(=C1)[N+](=O)[O-])O)O.NC=1SC=NN1>>S1C=2N(N=C1)C=C(N2)C2=CC(=C(C(O)=C2)O)[N+](=O)[O-] | [n:9]1[n:10][cH:11][s:12][c:13]1[NH2:14].O=[C:7]([c:6]1[cH:5][c:4]([N+:2](=[O:1])[O-:3])[c:18]([OH:19])[c:16]([OH:17])[cH:15]1)[CH2:8]Br>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6](-[c:7]2[cH:8][n:9]3[n:10][cH:11][s:12][c:13]3[n:14]2)[cH:15][c:16]([OH:17])[c:18]1[OH:19] | Nc1nncs1.O=C(CBr)c1cc(O)c(O)c([N+](=O)[O-])c1 | O=[N+]([O-])c1cc(-c2cn3ncsc3n2)cc(O)c1O | null | null | C(CCC)O | Aromatic Heterocycle Formation | OtherReaction | 1e7b60bd234328ab1e4f19fe6982e662049a41af5173258154148381b6929e0a | 9e77d52183fdbe84f0d2ab96039aaf521caea9340e743bdc6436175f1a3bbdb6 | c1ccc(-c2cn3ncsc3n2)cc1 | Br-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7].[NH2;D1;+0:8]-[c:9]1:[#16;a:10]:[c:11]:[#7;a:12]:[n;H0;D2;+0:13]:1>>[c:5]:[c:4]:[c;H0;D3;+0:3](-[c;H0;D3;+0:2]1:[cH;D2;+0:1]:[n;H0;D3;+0:13]2:[#7;a:12]:[c:11]:[#16;a:10]:[c:9]:2:[n;H0;D2;+0:8]:1):[c:6]:[c:7] | null | [] | null | null | null | null | A solution of 1.38 g of 2-bromo-3',4'-dihydroxy-5'-nitroacetophenone and 505.7 mg of 2-amino-1,3,4-thiadiazole in 25 ml of n-butanol is heated to boiling under reflux for 7 hours. The reaction mixture is then cooled to room temperature and the separated crystals are filtered under suction. There is obtained 5-(imidazo-... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Primary amine | null | c1nncs1 | c1cn2ncsc2n1 | c1ccccc1.c1cn2ncsc2n1 | HBr | C(CCC)O | null | null | Nc1nncs1.O=C(CBr)c1cc(O)c(O)c([N+](=O)[O-])c1>C(CCC)O>O=[N+]([O-])c1cc(-c2cn3ncsc3n2)cc(O)c1O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-716cf179f82c4a828949e3494182d303 | Nc1nccs1.O=C(CBr)c1cc(O)c(O)c([N+](=O)[O-])c1>>Br.O=[N+]([O-])c1cc(-c2cn3ccsc3n2)cc(O)c1O | BrCC(=O)C1=CC(=C(C(=C1)[N+](=O)[O-])O)O.NC=1SC=CN1>>Br.S1C=2N(C=C1)C=C(N2)C2=CC(=C(C(O)=C2)O)[N+](=O)[O-] | [n:10]1[cH:11][cH:12][s:13][c:14]1[NH2:15].O=[C:8]([c:7]1[cH:6][c:5]([N+:3](=[O:2])[O-:4])[c:19]([OH:20])[c:17]([OH:18])[cH:16]1)[CH2:9][Br:1]>>[BrH:1].[O:2]=[N+:3]([O-:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][n:10]3[cH:11][cH:12][s:13][c:14]3[n:15]2)[cH:16][c:17]([OH:18])[c:19]1[OH:20] | Nc1nccs1.O=C(CBr)c1cc(O)c(O)c([N+](=O)[O-])c1 | Br.O=[N+]([O-])c1cc(-c2cn3ccsc3n2)cc(O)c1O | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | fc4245e28231e2acdadf0a109add94d7bcbb15727aa9b3c4274dbbacfc4598a4 | 9e77d52183fdbe84f0d2ab96039aaf521caea9340e743bdc6436175f1a3bbdb6 | c1ccc(-c2cn3ccsc3n2)cc1 | O=[C;H0;D3;+0:1](-[CH2;D2;+0:2]-[Br;H0;D1;+0:3])-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8].[NH2;D1;+0:9]-[c:10]1:[#16;a:11]:[c:12]:[c:13]:[n;H0;D2;+0:14]:1>>[BrH;D0;+0:3].[c:6]:[c:5]:[c;H0;D3;+0:4](-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[n;H0;D3;+0:14]2:[c:13]:[c:12]:[#16;a:11]:[c:10]:2:[n;H0;D2;+0:9]:1):[c:7]:[c:8] | null | [] | null | null | null | null | A mixture of 2.78 g of 2-bromo-3',4'-dihydroxy-5'-nitroacetophenone, 1.01 g of 2-aminothiazole and 40 ml of ethanol is heated to boiling under reflux for 23 hours. The reaction mixture is then cooled to room temperature and the crystals are removed by filtration under suction. There is obtained 5-(imidazo[2,1-b]thiazol... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Primary amine | null | c1cscn1 | c1cn2ccsc2n1 | c1ccccc1.c1cn2ccsc2n1 | HO- | C(C)O | null | null | Nc1nccs1.O=C(CBr)c1cc(O)c(O)c([N+](=O)[O-])c1>C(C)O>Br.O=[N+]([O-])c1cc(-c2cn3ccsc3n2)cc(O)c1O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-aa4eda828af2427496961a45f8834596 | Nc1nc2ccccc2s1.O=C(CBr)c1cc(O)c(O)c([N+](=O)[O-])c1>>O=[N+]([O-])c1cc(-c2cn3c(n2)sc2ccccc23)cc(O)c1O | BrCC(=O)C1=CC(=C(C(=C1)[N+](=O)[O-])O)O.NC=1SC2=C(N1)C=CC=C2>>N=1C(=CN2C1SC1=C2C=CC=C1)C1=CC(=C(C(O)=C1)O)[N+](=O)[O-] | [n:9]1[c:10]([NH2:11])[s:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]12.O=[C:7]([c:6]1[cH:5][c:4]([N+:2](=[O:1])[O-:3])[c:22]([OH:23])[c:20]([OH:21])[cH:19]1)[CH2:8]Br>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6](-[c:7]2[cH:8][n:9]3[c:10]([n:11]2)[s:12][c:13]2[cH:14][cH:15][cH:16][cH:17][c:18]32)[cH:19][c:20]([OH:21])[c:22]1... | Nc1nc2ccccc2s1.O=C(CBr)c1cc(O)c(O)c([N+](=O)[O-])c1 | O=[N+]([O-])c1cc(-c2cn3c(n2)sc2ccccc23)cc(O)c1O | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 4e6c6daaf0a07588f0ef45f2229cd9b93389916c91afe110baae3a0ca1b93aaa | 9e77d52183fdbe84f0d2ab96039aaf521caea9340e743bdc6436175f1a3bbdb6 | c1ccc(-c2cn3c(n2)sc2ccccc23)cc1 | Br-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7].[NH2;D1;+0:8]-[c:9]1:[#16;a:10]:[c:11](:[c:12]):[c:13](:[c:14]):[n;H0;D2;+0:15]:1>>[c:12]:[c:11]1:[#16;a:10]:[c:9]2:[n;H0;D2;+0:8]:[c;H0;D3;+0:2](-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7]):[cH;D2;+0:1]:[n;H0;D3;+0:15]:2:[c:13]:1:[c:14] | null | [] | null | null | null | null | A mixture of 1.95 g of 2-bromo-3',4'-dihydroxy-5'-nitroacetophenone, 1.06 g of 2-aminobenzothiazole and 50 ml of ethanol is heated to boiling under reflux for 17 hours. The reaction mixture is then cooled to room temperature, whereupon the crystals are removed by filtration under suction. There is obtained 5-(imidazo[2... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Primary amine | null | c1ccc2scnc2c1 | c1ccc2c(c1)sc1nccn12 | c1ccccc1.c1ccc2c(c1)sc1nccn12 | HBr | C(C)O | null | null | Nc1nc2ccccc2s1.O=C(CBr)c1cc(O)c(O)c([N+](=O)[O-])c1>C(C)O>O=[N+]([O-])c1cc(-c2cn3c(n2)sc2ccccc23)cc(O)c1O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-0f27e377bd8d438882b4fdae17e1503a | Nc1ccccc1S.O=C(CBr)c1cc(O)c(O)c([N+](=O)[O-])c1>>O=[N+]([O-])c1cc(C2=Nc3ccccc3SC2)cc(O)c1O | BrCC(=O)C1=CC(=C(C(=C1)[N+](=O)[O-])O)O.NC1=C(C=CC=C1)S>>S1CC(=NC2=C1C=CC=C2)C2=CC(=C(C(O)=C2)O)[N+](=O)[O-] | [NH2:8][c:9]1[cH:10][cH:11][cH:12][cH:13][c:14]1[SH:15].O=[C:7]([c:6]1[cH:5][c:4]([N+:2](=[O:1])[O-:3])[c:20]([OH:21])[c:18]([OH:19])[cH:17]1)[CH2:16]Br>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6]([C:7]2=[N:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[S:15][CH2:16]2)[cH:17][c:18]([OH:19])[c:20]1[OH:21] | Nc1ccccc1S.O=C(CBr)c1cc(O)c(O)c([N+](=O)[O-])c1 | O=[N+]([O-])c1cc(C2=Nc3ccccc3SC2)cc(O)c1O | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 9abe984d79798f62298e20cb85803a2b6b66ccb662dd346e4027ed1ea73ef5e8 | 46f25929c54931666b6a40f7d6f3658a63ddb3ca3045c918b83969ec75c8cefa | c1ccc(C2=Nc3ccccc3SC2)cc1 | Br-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-[c:3](:[c:4]):[c:5].[NH2;D1;+0:6]-[c:7](:[c:8]):[c:9](-[SH;D1;+0:10]):[c:11]>>[c:8]:[c:7]1:[c:9](:[c:11])-[S;H0;D2;+0:10]-[CH2;D2;+0:1]-[C;H0;D3;+0:2](-[c:3](:[c:4]):[c:5])=[N;H0;D2;+0:6]-1 | null | [] | null | null | null | null | A mixture of 2.78 g of 2-bromo-3',4'-dihydroxy-5'-nitroacetophenone, 1.51 g of 2-aminothiophenol and 50 ml of ethanol is heated to boiling under reflux for 1 hour. The reaction mixture is then cooled to room temperature, whereupon the crystals are removed by filtration under suction. There is obtained 5-(2H-1,4-benzoth... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Primary amine.Aromatic thiol | Substituted imine.Monosulfide | null | C1=Nc2ccccc2SC1 | c1ccccc1.C1=Nc2ccccc2SC1 | HBr | C(C)O | null | null | Nc1ccccc1S.O=C(CBr)c1cc(O)c(O)c([N+](=O)[O-])c1>C(C)O>O=[N+]([O-])c1cc(C2=Nc3ccccc3SC2)cc(O)c1O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-422842edd6d34bde9ae227108fb09533 | Nc1ccccn1.O=C(CBr)c1cc(O)c(O)c([N+](=O)[O-])c1>>O=[N+]([O-])c1cc(-c2cnc3ccccn23)cc(O)c1O | BrCC(=O)C1=CC(=C(C(=C1)[N+](=O)[O-])O)O.NC1=NC=CC=C1>>N=1C=C(N2C1C=CC=C2)C2=CC(=C(C(O)=C2)O)[N+](=O)[O-] | [NH2:9][c:10]1[cH:11][cH:12][cH:13][cH:14][n:15]1.O=[C:7]([c:6]1[cH:5][c:4]([N+:2](=[O:1])[O-:3])[c:19]([OH:20])[c:17]([OH:18])[cH:16]1)[CH2:8]Br>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6](-[c:7]2[cH:8][n:9][c:10]3[cH:11][cH:12][cH:13][cH:14][n:15]23)[cH:16][c:17]([OH:18])[c:19]1[OH:20] | Nc1ccccn1.O=C(CBr)c1cc(O)c(O)c([N+](=O)[O-])c1 | O=[N+]([O-])c1cc(-c2cnc3ccccn23)cc(O)c1O | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 98b9b4632b0457bc035e4a4d36e0a1658474c53cb0def2f4c4d097bbd0d48009 | 9e77d52183fdbe84f0d2ab96039aaf521caea9340e743bdc6436175f1a3bbdb6 | c1ccc(-c2cnc3ccccn23)cc1 | Br-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7].[NH2;D1;+0:8]-[c:9](:[c:10]):[n;H0;D2;+0:11]:[c:12]:[c:13]>>[c:10]:[c:9]1:[n;H0;D2;+0:8]:[cH;D2;+0:1]:[c;H0;D3;+0:2](-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7]):[n;H0;D3;+0:11]:1:[c:12]:[c:13] | null | [] | null | null | null | null | A mixture of 987.5 mg of 2-bromo-3',4'-dihydroxy-5'-nitroacetophenone and 1.01 g of 2-aminopyridine is melted at 110°. After 30 minutes the melt is treated with 15 ml of ethanol and heated to boiling under reflux for 3 hours. The reaction mixture is then cooled to room temperature and the crystals are removed by filtra... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Primary amine | null | c1ccncc1 | c1ccn2ccnc2c1 | c1ccccc1.c1ccn2ccnc2c1 | HBr | C(C)O | null | null | Nc1ccccn1.O=C(CBr)c1cc(O)c(O)c([N+](=O)[O-])c1>C(C)O>O=[N+]([O-])c1cc(-c2cnc3ccccn23)cc(O)c1O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-4db6d753b5ac478ebefe1fd4ffa9c9f7 | CC(C)(C)NC(=O)OCCCCCCN.COc1cc(C(=O)O)cc([N+](=O)[O-])c1O>>COc1cc(C(=O)NCCCCCCOC(=O)NC(C)(C)C)cc([N+](=O)[O-])c1O | NCCCCCCOC(NC(C)(C)C)=O.C(=O)(N1C=NC=C1)N1C=NC=C1.OC1=C(C=C(C(=O)O)C=C1[N+](=O)[O-])OC>>OC1=C(C=C(C(=O)NCCCCCCOC(NC(C)(C)C)=O)C=C1[N+](=O)[O-])OC | [NH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][C:16](=[O:17])[NH:18][C:19]([CH3:20])([CH3:21])[CH3:22].O[C:6]([c:5]1[cH:4][c:3]([O:2][CH3:1])[c:28]([OH:29])[c:24]([N+:25](=[O:26])[O-:27])[cH:23]1)=[O:7]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15]... | CC(C)(C)NC(=O)OCCCCCCN.COc1cc(C(=O)O)cc([N+](=O)[O-])c1O | COc1cc(C(=O)NCCCCCCOC(=O)NC(C)(C)C)cc([N+](=O)[O-])c1O | null | null | O1CCCC1 | Acylation | Carboxylic acid with primary amine to amide | 37494d655fc476b499cf056f6435518833ae87795aab58744c3c61cc6e2d35e8 | 1acc31e468ee9ff2d6601bea2d2eb10c464508bb7150073479303b3753dd92b4 | c1ccccc1 | O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[C:7]-[NH2;D1;+0:8]>>[C:6]-[C:7]-[NH;D2;+0:8]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 15 | MINUTE | 8.9 g of 1,1'-carbonyldiimidazole are added to a solution of 10.7 g of 4-hydroxy-3-methoxy-5-nitrobenzoic acid in 500 ml of dry tetrahydrofuran and the reaction mixture is subsequently heated to 65°-70° for 5 hours. It is then cooled to room temperature and a solution of 21.6 g of 6-aminohexyl-t-butylcarbamate in 50 ml... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Primary amine | Secondary amide | null | null | c1ccccc1 | HO- | O1CCCC1 | null | 0.25 | CC(C)(C)NC(=O)OCCCCCCN.COc1cc(C(=O)O)cc([N+](=O)[O-])c1O>O1CCCC1>COc1cc(C(=O)NCCCCCCOC(=O)NC(C)(C)C)cc([N+](=O)[O-])c1O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-763f5cf1be4d4681a4528ca429a6d06b | BrB(Br)Br.COc1cc(C(=O)NCCCCCCN)cc([N+](=O)[O-])c1O>>Br.NCCCCCCNC(=O)c1cc(O)c(O)c([N+](=O)[O-])c1 | B(Br)(Br)Br.Br.NCCCCCCNC(C1=CC(=C(C(=C1)[N+](=O)[O-])O)OC)=O>>Br.NCCCCCCNC(C1=CC(=C(C(=C1)[N+](=O)[O-])O)O)=O | BrB(Br)[Br:1].C[O:15][c:14]1[cH:13][c:12]([C:10]([NH:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][NH2:2])=[O:11])[cH:22][c:18]([N+:19](=[O:20])[O-:21])[c:16]1[OH:17]>>[BrH:1].[NH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10](=[O:11])[c:12]1[cH:13][c:14]([OH:15])[c:16]([OH:17])[c:18]([N+:19](=[O:20])[O-:21])... | BrB(Br)Br.COc1cc(C(=O)NCCCCCCN)cc([N+](=O)[O-])c1O | Br.NCCCCCCNC(=O)c1cc(O)c(O)c([N+](=O)[O-])c1 | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | 005318874c4792a3ed14897fb19099f1f6e548b285f476e19a15213a92356c2d | 0bab01685da92cdead9c84b3a9c513c0e9bd4114585991beae2460d8c47b3623 | c1ccccc1 | Br-B(-Br)-[Br;H0;D1;+0:1].C-[O;H0;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[BrH;D0;+0:1].[OH;D1;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | 17 | HOUR | 1.25 g of boron tribromide are added -20° to a suspension of 392.3 mg of N-(6-aminohexyl)-4-hydroxy-5-nitro-m-anisamide hydrobromide in 25 ml of dry methylene chloride. After the addition the mixture is stirred at -20° for 1 hour and subsequently at room temperature for 17 hours. The reaction mixture is then evaporated... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1 | HBr.B | C(Cl)Cl | null | 17 | BrB(Br)Br.COc1cc(C(=O)NCCCCCCN)cc([N+](=O)[O-])c1O>C(Cl)Cl>Br.NCCCCCCNC(=O)c1cc(O)c(O)c([N+](=O)[O-])c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-f4fc15ce92b14b159ec159faa53d9ef5 | COc1cc(C=O)cc([N+](=O)[O-])c1O.Nc1ccccc1N>>COc1cc(-c2nc3ccccc3[nH]2)cc([N+](=O)[O-])c1O | [N+](=O)([O-])C=1C(=C(C=C(C=O)C1)OC)O.C1(=C(C=CC=C1)N)N>>N1=C(NC2=C1C=CC=C2)C2=CC(=C(C(=C2)[N+](=O)[O-])O)OC | O=[CH:6][c:5]1[cH:4][c:3]([O:2][CH3:1])[c:20]([OH:21])[c:16]([N+:17](=[O:18])[O-:19])[cH:15]1.[NH2:7][c:8]1[cH:9][cH:10][cH:11][cH:12][c:13]1[NH2:14]>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]3[cH:9][cH:10][cH:11][cH:12][c:13]3[nH:14]2)[cH:15][c:16]([N+:17](=[O:18])[O-:19])[c:20]1[OH:21] | COc1cc(C=O)cc([N+](=O)[O-])c1O.Nc1ccccc1N | COc1cc(-c2nc3ccccc3[nH]2)cc([N+](=O)[O-])c1O | null | null | [N+](=O)([O-])C1=CC=CC=C1.CO | Aromatic Heterocycle Formation | Benzimidazole aldehyde | 357211f0cea48f6066cc617c063d8f639b186739754abf69a9bef955d42b7d06 | 947e8e758a50553bad3d8f39fd1540e5051c4c73055f7a5a9da00894523e8ba0 | c1ccc(-c2nc3ccccc3[nH]2)cc1 | O=[CH;D2;+0:1]-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6].[NH2;D1;+0:7]-[c:8](:[c:9]):[c:10](-[NH2;D1;+0:11]):[c:12]>>[c:9]:[c:8]1:[nH;D2;+0:7]:[c;H0;D3;+0:1](-[c;H0;D3;+0:2](:[c:3]:[c:4]):[c:5]:[c:6]):[n;H0;D2;+0:11]:[c:10]:1:[c:12] | null | [] | null | null | 15 | MINUTE | aa) A solution of 4.93 g of 5-nitrovanillin and 2.7 g of 1,2-phenylenediamine in 45 ml of methanol and 15 ml of nitrobenzene is heated to boiling under reflux. After 15 minutes crystals begin to separate from the red solution. After 18 hours the reaction mixture is cooled to room temperature and diluted with 60 ml of m... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine.Primary amine | null | c1ccccc1 | c1ccc2[nH]cnc2c1 | c1ccccc1.c1ccc2[nH]cnc2c1 | HO- | [N+](=O)([O-])C1=CC=CC=C1.CO | null | 0.25 | COc1cc(C=O)cc([N+](=O)[O-])c1O.Nc1ccccc1N>[N+](=O)([O-])C1=CC=CC=C1.CO>COc1cc(-c2nc3ccccc3[nH]2)cc([N+](=O)[O-])c1O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-eef274ee9c37415f8062482eecdc822a | COc1cc(-c2nc3ccccc3[nH]2)cc([N+](=O)[O-])c1O>>O=[N+]([O-])c1cc(-c2nc3ccccc3[nH]2)cc(O)c1O | N1=C(NC2=C1C=CC=C2)C2=CC(=C(C(=C2)[N+](=O)[O-])O)OC>>N1=C(NC2=C1C=CC=C2)C2=CC(=C(C(O)=C2)O)[N+](=O)[O-] | C[O:18][c:17]1[cH:16][c:6](-[c:7]2[n:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[nH:15]2)[cH:5][c:4]([N+:2](=[O:1])[O-:3])[c:19]1[OH:20]>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6](-[c:7]2[n:8][c:9]3[cH:10][cH:11][cH:12][cH:13][c:14]3[nH:15]2)[cH:16][c:17]([OH:18])[c:19]1[OH:20] | COc1cc(-c2nc3ccccc3[nH]2)cc([N+](=O)[O-])c1O | O=[N+]([O-])c1cc(-c2nc3ccccc3[nH]2)cc(O)c1O | null | null | C(C)(=O)O.Br | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc(-c2nc3ccccc3[nH]2)cc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | A suspension of 860.1 mg of 4-(2-benzimidazolyl)-2-methoxy-6-nitrophenol in 10 ml of glacial acetic acid and 10 ml of 48 percent hydrobromic acid is heated to boiling under reflux for 72 hours. The mixture is then evaporated and the residue is treated four times with 50 ml of toluene each time, which is again distilled... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.c1ccc2[nH]cnc2c1 | Other | C(C)(=O)O.Br | null | null | COc1cc(-c2nc3ccccc3[nH]2)cc([N+](=O)[O-])c1O>C(C)(=O)O.Br>O=[N+]([O-])c1cc(-c2nc3ccccc3[nH]2)cc(O)c1O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-d47a97c87f014cceaa61652c5d099966 | COc1cc(C(=O)CBr)cc([N+](=O)[O-])c1O>>O=C(CBr)c1cc(O)c(O)c([N+](=O)[O-])c1 | BrCC(=O)C1=CC(=C(C(=C1)[N+](=O)[O-])O)OC.B(Br)(Br)Br>>BrCC(=O)C1=CC(=C(C(=C1)[N+](=O)[O-])O)O | C[O:8][c:7]1[cH:6][c:5]([C:2](=[O:1])[CH2:3][Br:4])[cH:15][c:11]([N+:12](=[O:13])[O-:14])[c:9]1[OH:10]>>[O:1]=[C:2]([CH2:3][Br:4])[c:5]1[cH:6][c:7]([OH:8])[c:9]([OH:10])[c:11]([N+:12](=[O:13])[O-:14])[cH:15]1 | COc1cc(C(=O)CBr)cc([N+](=O)[O-])c1O | O=C(CBr)c1cc(O)c(O)c([N+](=O)[O-])c1 | null | null | C(Cl)Cl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccccc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 16 | HOUR | A suspension of 29.0 g of 2-bromo-4'-hydroxy-3'-methoxy-5'-nitroacetophenone in 700 ml of dry methylene chloride is treated at -20° within 30 minutes with a solution of 125.3 g of boron tribromide in 300 ml of dry methylene chloride. After the addition the mixture is stirred at -20° for a further 1 hour and at room tem... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1 | Other | C(Cl)Cl | null | 16 | COc1cc(C(=O)CBr)cc([N+](=O)[O-])c1O>C(Cl)Cl>O=C(CBr)c1cc(O)c(O)c([N+](=O)[O-])c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-0c8993df9b0641b8ace69a9cf1006bc2 | O=S(=O)(O)O.O=[N+]([O-])c1cc(O)c(O)c([N+](=O)[O-])c1>>CCC(=O)Oc1cc([N+](=O)[O-])cc([N+](=O)[O-])c1OC(=O)CC | [N+](=O)([O-])C1=C(C(O)=CC(=C1)[N+](=O)[O-])O.S(O)(O)(=O)=O>>C(CC)(=O)OC1=C(C(=CC(=C1)[N+](=O)[O-])[N+](=O)[O-])OC(CC)=O | O=S(=O)([OH:4])[OH:20].[c:1]1([N+:9](=[O:10])[O-:11])[cH:7][c:6]([OH:5])[c:17]([OH:18])[c:13]([N+:14](=[O:15])[O-:16])[cH:12]1>>[CH3:1][CH2:2][C:3](=[O:4])[O:5][c:6]1[cH:7][c:8]([N+:9](=[O:10])[O-:11])[cH:12][c:13]([N+:14](=[O:15])[O-:16])[c:17]1[O:18][C:19](=[O:20])[CH2:21][CH3:22] | O=S(=O)(O)O.O=[N+]([O-])c1cc(O)c(O)c([N+](=O)[O-])c1 | CCC(=O)Oc1cc([N+](=O)[O-])cc([N+](=O)[O-])c1OC(=O)CC | null | null | C(CC)(=O)OC(CC)=O | Acylation | OtherReaction | e958db7110073a07179f1cd6fa0d731f686f653a751ce5570fe9544c739e0f84 | 2da882113ce860557941d34be45cede751b3a8f086d3e064860b56c2dec105fe | c1ccccc1 | O=S(=O)(-[OH;D1;+0:1])-[OH;D1;+0:2].[#7;+:3]-[c:4]1:[cH;D2;+0:5]:[c;H0;D3;+0:6](-[N+;H0;D3:7](-[O;-;D1;H0:8])=[O;D1;H0:9]):[cH;D2;+0:10]:[c:11](-[OH;D1;+0:12]):[c:13]:1-[OH;D1;+0:14]>>[#7;+:3]-[c:4]1:[cH;D2;+0:5]:[c:15](-[N+;H0;D3:7](-[O;-;D1;H0:8])=[O;D1;H0:9]):[cH;D2;+0:10]:[c:11](-[O;H0;D2;+0:12]-[C:16](=[O;H0;D1;+0... | null | [] | null | null | null | null | A solution of 2.0 g of 3,5-dinitropyrocatechol in 25 ml of propionic anhydride is heated at 110° for 18 hours in the presence of a catalytic amount of conc. sulfuric acid, the excess anhydride is distilled off at 70° in a high vacuum (1.33 Pa), the residue is dissolved in methylene chloride, washed with water, dried ov... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group.Aromatic alcohol.Aromatic alcohol | Ester.Ester.Nitro group | c1ccccc1 | c1ccccc1 | c1ccccc1 | null | C(CC)(=O)OC(CC)=O | null | null | O=S(=O)(O)O.O=[N+]([O-])c1cc(O)c(O)c([N+](=O)[O-])c1>C(CC)(=O)OC(CC)=O>CCC(=O)Oc1cc([N+](=O)[O-])cc([N+](=O)[O-])c1OC(=O)CC |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-e31611279f604f9ebc0467b4d9506a18 | CC(=O)[O-].O=C(CBr)c1cc(O)c(O)c([N+](=O)[O-])c1>>CC(=O)OCC(=O)c1cc(O)c(O)c([N+](=O)[O-])c1 | C(C)(=O)[O-].[Na+].BrCC(=O)C1=CC(=C(C(=C1)[N+](=O)[O-])O)O>>C(C)(=O)OCC(C1=CC(=C(C(=C1)[N+](=O)[O-])O)O)=O | [CH3:1][C:2](=[O:3])[O-:4].Br[CH2:5][C:6](=[O:7])[c:8]1[cH:9][c:10]([OH:11])[c:12]([OH:13])[c:14]([N+:15](=[O:16])[O-:17])[cH:18]1>>[CH3:1][C:2](=[O:3])[O:4][CH2:5][C:6](=[O:7])[c:8]1[cH:9][c:10]([OH:11])[c:12]([OH:13])[c:14]([N+:15](=[O:16])[O-:17])[cH:18]1 | CC(=O)[O-].O=C(CBr)c1cc(O)c(O)c([N+](=O)[O-])c1 | CC(=O)OCC(=O)c1cc(O)c(O)c([N+](=O)[O-])c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 3363815125740436deee4d4949cd72b71b05d6b4f93b49b4174365a783885b33 | 7abea7b36487848edf19908b17071379ab599411cde2e67ec42a2a4a6c97dffd | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[C;D1;H3:5]-[C:6](-[O-;H0;D1:7])=[O;D1;H0:8]>>[C;D1;H3:5]-[C:6](=[O;D1;H0:8])-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4] | null | [] | null | null | 6 | HOUR | 1.26 g of sodium acetate are added to a solution of 1.35 g of 2-bromo-3',4'-dihydroxy-5'-nitroacetophenone in 25 ml of alcohol and heated to boiling under reflux. After 6 hours, the reaction mixture is filtered from separated sodium bromide and evaporated. The residue is dissolved in ethyl acetate. The solution is wash... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone | Ketone.Ester | null | null | c1ccccc1 | Br- | null | null | 6 | CC(=O)[O-].O=C(CBr)c1cc(O)c(O)c([N+](=O)[O-])c1>>CC(=O)OCC(=O)c1cc(O)c(O)c([N+](=O)[O-])c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-4cc8e769281a43ad8c89fe898fb417f7 | NC(=S)c1cccnc1.O=C(CBr)c1cc(O)c(O)c([N+](=O)[O-])c1>>O=[N+]([O-])c1cc(-c2csc(-c3cccnc3)n2)cc(O)c1O | BrCC(=O)C1=CC(=C(C(=C1)[N+](=O)[O-])O)O.C(C1=CN=CC=C1)(=S)N>>[N+](=O)([O-])C1=C(C(O)=CC(=C1)C=1N=C(SC1)C=1C=NC=CC1)O | [S:9]=[C:10]([c:11]1[cH:12][cH:13][cH:14][n:15][cH:16]1)[NH2:17].O=[C:7]([c:6]1[cH:5][c:4]([N+:2](=[O:1])[O-:3])[c:21]([OH:22])[c:19]([OH:20])[cH:18]1)[CH2:8]Br>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6](-[c:7]2[cH:8][s:9][c:10](-[c:11]3[cH:12][cH:13][cH:14][n:15][cH:16]3)[n:17]2)[cH:18][c:19]([OH:20])[c:21]1[OH:22] | NC(=S)c1cccnc1.O=C(CBr)c1cc(O)c(O)c([N+](=O)[O-])c1 | O=[N+]([O-])c1cc(-c2csc(-c3cccnc3)n2)cc(O)c1O | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 21eb8c7cda3c7fc14309a0c556334226f1a9147c334386d33bc70341830a82ec | 9f145257a80f08f1a7a6ee36c84cd4115965bd63128f36de61c7ed688ad2603c | c1ccc(-c2csc(-c3cccnc3)n2)cc1 | Br-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=O)-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7].[NH2;D1;+0:8]-[C;H0;D3;+0:9](=[S;H0;D1;+0:10])-[c;H0;D3;+0:11]1:[c:12]:[c:13]:[c:14]:[#7;a:15]:[c:16]:1>>[c:5]:[c:4]:[c;H0;D3;+0:3](-[c;H0;D3;+0:2]1:[cH;D2;+0:1]:[s;H0;D2;+0:10]:[c;H0;D3;+0:9](-[c;H0;D3;+0:11]2:[c:12]:[c:13]:[c:14]:[#7;a:15]:[... | null | [] | null | null | null | null | A suspension of 2.91 g of 2-bromo-3',4'-dihydroxy-5'-nitroacetophenone is treated with 1.31 g of thionicotinamide in 50 ml of alcohol and heated to boiling under reflux for 2 hours. After cooling to room temperature the crystals are filtered under suction and recrystallized from N,N-dimethylformamide/alcohol. There is ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Thioamide | null | null | c1cscn1 | c1ccccc1.c1cscn1.c1ccncc1 | HBr | null | null | null | NC(=S)c1cccnc1.O=C(CBr)c1cc(O)c(O)c([N+](=O)[O-])c1>>O=[N+]([O-])c1cc(-c2csc(-c3cccnc3)n2)cc(O)c1O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-aea1dba770b54ddda72d118a6afff955 | NCC(=O)c1ccccc1.O=C(CBr)c1cc(O)c(O)c([N+](=O)[O-])c1>>Cc1c(C(=O)c2cc(O)c(O)c([N+](=O)[O-])c2)[nH]c2ccccc12 | BrCC(=O)C1=CC(=C(C(=C1)[N+](=O)[O-])O)O.NCC(=O)C1=CC=CC=C1.CN(C=O)C>>OC=1C=C(C(=O)C=2NC3=CC=CC=C3C2C)C=C(C1O)[N+](=O)[O-] | O=[C:2]([CH2:3][NH2:17])[c:23]1[cH:18][cH:19][cH:20][cH:21][cH:22]1.Br[CH2:1][C:4](=[O:5])[c:6]1[cH:7][c:8]([OH:9])[c:10]([OH:11])[c:12]([N+:13](=[O:14])[O-:15])[cH:16]1>>[CH3:1][c:2]1[c:3]([C:4](=[O:5])[c:6]2[cH:7][c:8]([OH:9])[c:10]([OH:11])[c:12]([N+:13](=[O:14])[O-:15])[cH:16]2)[nH:17][c:18]2[cH:19][cH:20][cH:21][c... | NCC(=O)c1ccccc1.O=C(CBr)c1cc(O)c(O)c([N+](=O)[O-])c1 | Cc1c(C(=O)c2cc(O)c(O)c([N+](=O)[O-])c2)[nH]c2ccccc12 | null | null | null | Aromatic Heterocycle Formation | OtherReaction | 7501a2075c131a5a697be83b8893b35998b6f93f2cc7dbe47176bf49df74cf51 | 56ed520f4f13c3550ff850cebe88b7872ea827a3d10cfa555c019deb4ba80564 | O=C(c1ccccc1)c1cc2ccccc2[nH]1 | Br-[CH2;D2;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6].O=[C;H0;D3;+0:7](-[CH2;D2;+0:8]-[NH2;D1;+0:9])-[c:10](:[c:11]):[cH;D2;+0:12]:[c:13]:[c:14]>>[CH3;D1;+0:1]-[c;H0;D3;+0:7]1:[c:10](:[c:11]):[c;H0;D3;+0:12](:[c:13]:[c:14]):[nH;D2;+0:9]:[c;H0;D3;+0:8]:1-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | null | null | A solution of 5.52 g of 2-bromo-3',4'-dihydroxy-5'-nitroacetophenone and 2.7 g of 2-aminoacetophenone in 100 ml of dry N,N-dimethylformamide is stirred at 90° for 24 hours. The reaction mixture is evaporated, the residue is dissolved in ethyl acetate, washed with water, dried over sodium sulfate, filtered and evaporate... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Ketone.Primary amine | Ketone | c1ccccc1 | c1ccc2[nH]ccc2c1 | c1ccccc1.c1ccc2[nH]ccc2c1 | HBr | null | null | null | NCC(=O)c1ccccc1.O=C(CBr)c1cc(O)c(O)c([N+](=O)[O-])c1>>Cc1c(C(=O)c2cc(O)c(O)c([N+](=O)[O-])c2)[nH]c2ccccc12 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ac0433796e55403c8260e8da36a03b90 | NC(=S)Nc1cccnc1.O=C(CBr)c1cc(O)c(O)c([N+](=O)[O-])c1>>Br.O=[N+]([O-])c1cc(-c2csc(Nc3cccnc3)n2)cc(O)c1O | BrCC(=O)C1=CC(=C(C(=C1)[N+](=O)[O-])O)O.N1=CC(=CC=C1)NC(=S)N>>Br.[N+](=O)([O-])C1=C(C(O)=CC(=C1)C=1N=C(SC1)NC=1C=NC=CC1)O | [S:10]=[C:11]([NH:12][c:13]1[cH:14][cH:15][cH:16][n:17][cH:18]1)[NH2:19].O=[C:8]([c:7]1[cH:6][c:5]([N+:3](=[O:2])[O-:4])[c:23]([OH:24])[c:21]([OH:22])[cH:20]1)[CH2:9][Br:1]>>[BrH:1].[O:2]=[N+:3]([O-:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][s:10][c:11]([NH:12][c:13]3[cH:14][cH:15][cH:16][n:17][cH:18]3)[n:19]2)[cH:20][c:21]([O... | NC(=S)Nc1cccnc1.O=C(CBr)c1cc(O)c(O)c([N+](=O)[O-])c1 | Br.O=[N+]([O-])c1cc(-c2csc(Nc3cccnc3)n2)cc(O)c1O | null | null | C(CCC)O | Aromatic Heterocycle Formation | OtherReaction | bef473efef1d9ea696235ac9e0e73338149dac4bc5d824d8ecb15263a8e3a4b0 | 39fbe568f79251ca2d63e869c3b1ee705fef7458c6d99863e8f91d4da02df595 | c1ccc(-c2csc(Nc3cccnc3)n2)cc1 | O=[C;H0;D3;+0:1](-[CH2;D2;+0:2]-[Br;H0;D1;+0:3])-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8].[#7;a:9]:[c:10]:[c:11]-[#7:12]-[C;H0;D3;+0:13](-[NH2;D1;+0:14])=[S;H0;D1;+0:15]>>[#7;a:9]:[c:10]:[c:11]-[#7:12]-[c;H0;D3;+0:13]1:[n;H0;D2;+0:14]:[c;H0;D3;+0:1](-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8]):[cH;D2;+0:2]:[s;H0;D2;+0:15... | null | [] | null | null | null | null | A suspension of 7.32 g of 2-bromo-3',4'-dihydroxy-5'-nitroacetophenone is treated with 4.06 g of 1-(3-pyridinyl)-2-thiourea in 100 ml of n-butanol and heated to boiling under reflux for 3 hours. After cooling to room temperature the crystals are filtered under suction and recrystallized from n-butanol. There is obtaine... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Thiourea | null | null | c1cscn1 | c1ccccc1.c1cscn1.c1ccncc1 | HO- | C(CCC)O | null | null | NC(=S)Nc1cccnc1.O=C(CBr)c1cc(O)c(O)c([N+](=O)[O-])c1>C(CCC)O>Br.O=[N+]([O-])c1cc(-c2csc(Nc3cccnc3)n2)cc(O)c1O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-40bbc20683f34810be7343d13e76ba79 | NC(=S)Nc1cnc2ccccc2c1.O=C(CBr)c1cc(O)c(O)c([N+](=O)[O-])c1>>Br.O=[N+]([O-])c1cc(-c2csc(Nc3cnc4ccccc4c3)n2)cc(O)c1O | BrCC(=O)C1=CC(=C(C(=C1)[N+](=O)[O-])O)O.N1=CC(=CC2=CC=CC=C12)NC(=S)N>>Br.[N+](=O)([O-])C1=C(C(O)=CC(=C1)C=1N=C(SC1)NC=1C=NC2=CC=CC=C2C1)O | [S:10]=[C:11]([NH:12][c:13]1[cH:14][n:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[cH:22]1)[NH2:23].O=[C:8]([c:7]1[cH:6][c:5]([N+:3](=[O:2])[O-:4])[c:27]([OH:28])[c:25]([OH:26])[cH:24]1)[CH2:9][Br:1]>>[BrH:1].[O:2]=[N+:3]([O-:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][s:10][c:11]([NH:12][c:13]3[cH:14][n:15][c:16]4[cH:17][cH:1... | NC(=S)Nc1cnc2ccccc2c1.O=C(CBr)c1cc(O)c(O)c([N+](=O)[O-])c1 | Br.O=[N+]([O-])c1cc(-c2csc(Nc3cnc4ccccc4c3)n2)cc(O)c1O | null | null | C(CCC)O | Aromatic Heterocycle Formation | OtherReaction | bef473efef1d9ea696235ac9e0e73338149dac4bc5d824d8ecb15263a8e3a4b0 | 39fbe568f79251ca2d63e869c3b1ee705fef7458c6d99863e8f91d4da02df595 | c1ccc(-c2csc(Nc3cnc4ccccc4c3)n2)cc1 | O=[C;H0;D3;+0:1](-[CH2;D2;+0:2]-[Br;H0;D1;+0:3])-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8].[#7;a:9]:[c:10]:[c:11]-[#7:12]-[C;H0;D3;+0:13](-[NH2;D1;+0:14])=[S;H0;D1;+0:15]>>[#7;a:9]:[c:10]:[c:11]-[#7:12]-[c;H0;D3;+0:13]1:[n;H0;D2;+0:14]:[c;H0;D3;+0:1](-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8]):[cH;D2;+0:2]:[s;H0;D2;+0:15... | null | [] | null | null | null | null | A suspension of 6.35 g of 2-bromo-3',4'-dihydroxy-5'-nitroacetophenone is treated with 4.68 g of 1-(3-quinolinyl)-2-thiourea in 150 ml of n-butanol and heated to boiling under reflux for 3 hours. After cooling to room temperature the crystals are filtered under suction and recrystallized from n-butanol. There is obtain... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Thiourea | null | null | c1cscn1 | c1ccccc1.c1cscn1.c1ccc2ncccc2c1 | HO- | C(CCC)O | null | null | NC(=S)Nc1cnc2ccccc2c1.O=C(CBr)c1cc(O)c(O)c([N+](=O)[O-])c1>C(CCC)O>Br.O=[N+]([O-])c1cc(-c2csc(Nc3cnc4ccccc4c3)n2)cc(O)c1O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-2dbf33c8885b471994c71536e7de1ad1 | CC(=O)CCCCC(=O)Nc1ccc(C(F)(F)F)cc1.O=Cc1cc(O)c(O)c([N+](=O)[O-])c1>>O=C(/C=C/c1cc(O)c(O)c([N+](=O)[O-])c1)CCCCC(=O)Nc1ccc(C(F)(F)F)cc1 | N1CCCC1.C(C)(=O)O.OC=1C=C(C=O)C=C(C1O)[N+](=O)[O-].O=C(CCCCC(=O)NC1=CC=C(C=C1)C(F)(F)F)C>>OC=1C=C(C=C(C1O)[N+](=O)[O-])/C=C/C(CCCCC(=O)NC1=CC=C(C=C1)C(F)(F)F)=O | [O:1]=[C:2]([CH3:3])[CH2:16][CH2:17][CH2:18][CH2:19][C:20](=[O:21])[NH:22][c:23]1[cH:24][cH:25][c:26]([C:27]([F:28])([F:29])[F:30])[cH:31][cH:32]1.O=[CH:4][c:5]1[cH:6][c:7]([OH:8])[c:9]([OH:10])[c:11]([N+:12](=[O:13])[O-:14])[cH:15]1>>[O:1]=[C:2](/[CH:3]=[CH:4]/[c:5]1[cH:6][c:7]([OH:8])[c:9]([OH:10])[c:11]([N+:12](=[O:... | CC(=O)CCCCC(=O)Nc1ccc(C(F)(F)F)cc1.O=Cc1cc(O)c(O)c([N+](=O)[O-])c1 | O=C(/C=C/c1cc(O)c(O)c([N+](=O)[O-])c1)CCCCC(=O)Nc1ccc(C(F)(F)F)cc1 | null | null | O1CCCC1 | C-C Coupling | Aldehyde and ketone to alpha,beta-unsaturated carbonyl | df1bdbab1a06af9561d74fe6bc94ee8bda1d14faad9db1ada3a214bd64a24cf8 | c93e93ada40f7f922a54fe24d38f540ecf5ff25d55d497f79f5f400f75d0c7ae | O=C(/C=C/c1ccccc1)CCCCC(=O)Nc1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[C:5]-[C:6](-[CH3;D1;+0:7])=[O;D1;H0:8]>>[C:5]-[C:6](=[O;D1;H0:8])/[CH;D2;+0:7]=[CH;D2;+0:1]/[c:2](:[c:3]):[c:4] | null | [] | null | null | 56 | HOUR | 0.875 ml of pyrrolidine in 35 ml of tetrahydrofuran is treated at 5° with 0.605 ml of acetic acid and subsequently with 1.73 g of 3,4-dihydroxy-5-nitrobenzaldehyde and 2.87 g of 6-oxo-4'-(trifluoromethyl)-heptananilide and stirred at 23° under argon for 56 hours. The residue obtained after evaporating the reaction mixt... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Ketone | Ketone | null | null | c1ccccc1.c1ccccc1 | HO- | O1CCCC1 | null | 56 | CC(=O)CCCCC(=O)Nc1ccc(C(F)(F)F)cc1.O=Cc1cc(O)c(O)c([N+](=O)[O-])c1>O1CCCC1>O=C(/C=C/c1cc(O)c(O)c([N+](=O)[O-])c1)CCCCC(=O)Nc1ccc(C(F)(F)F)cc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-11253989ecdd47d6af93039717eb7e1b | CC(=O)OC(C)=O.COc1ccc(C=O)c(Cl)c1O>>COc1ccc(C=O)c(Cl)c1OC(C)=O | ClC1=C(C=O)C=CC(=C1O)OC.C(C)(=O)OC(C)=O>>C(C)(=O)OC1=C(C(=CC=C1OC)C=O)Cl | CC(=O)O[C:13]([CH3:14])=[O:15].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]=[O:8])[c:9]([Cl:10])[c:11]1[OH:12]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]=[O:8])[c:9]([Cl:10])[c:11]1[O:12][C:13]([CH3:14])=[O:15] | CC(=O)OC(C)=O.COc1ccc(C=O)c(Cl)c1O | COc1ccc(C=O)c(Cl)c1OC(C)=O | null | null | N1=CC=CC=C1 | Acylation | Acetic anhydride and alcohol to ester | 55f321cc520ab80a97c517ea4db1ffe6ba0ea312e2db70f74b0966421bec0a44 | 96218bff9f96200922f4dff3481116557fe6986cba41ef7bff8cc8a0b43bd224 | c1ccccc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | 8 | HOUR | 26.0 g of 2-chloro-3-hydroxy-p-anisaldehyde are dissolved in 400 ml of acetic anhydride and 5 ml of pyridine. The solution is stirred at 80° for 8 hours, subsequently evaporated, the residue is partitioned between ice-water and methylene chloride, the organic phase is dried over sodium sulfate, evaporated and the resid... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Aromatic alcohol | Ester | null | null | c1ccccc1 | HO- | N1=CC=CC=C1 | null | 8 | CC(=O)OC(C)=O.COc1ccc(C=O)c(Cl)c1O>N1=CC=CC=C1>COc1ccc(C=O)c(Cl)c1OC(C)=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-137eeaa7b8d44e5e804371b94cba8f68 | COc1ccc(C=O)c(Cl)c1OC(C)=O.O=[N+]([O-])O>>COc1c([N+](=O)[O-])cc(C=O)c(Cl)c1OC(C)=O | C(C)(=O)OC1=C(C(=CC=C1OC)C=O)Cl.[N+](=O)(O)[O-]>>C(C)(=O)OC1=C(C(=CC(=C1OC)[N+](=O)[O-])C=O)Cl | [CH3:1][O:2][c:3]1[cH:4][cH:8][c:9]([CH:10]=[O:11])[c:12]([Cl:13])[c:14]1[O:15][C:16]([CH3:17])=[O:18].O[N+:5](=[O:6])[O-:7]>>[CH3:1][O:2][c:3]1[c:4]([N+:5](=[O:6])[O-:7])[cH:8][c:9]([CH:10]=[O:11])[c:12]([Cl:13])[c:14]1[O:15][C:16]([CH3:17])=[O:18] | COc1ccc(C=O)c(Cl)c1OC(C)=O.O=[N+]([O-])O | COc1c([N+](=O)[O-])cc(C=O)c(Cl)c1OC(C)=O | null | null | null | Functional Group Addition | Aromatic nitration with HNO3 | 53848b8b2bb4e867226e49db2e60519b24be9379900e3ad7c56af54fe8fde7a5 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | c1ccccc1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[#8:4]-[c:5](:[c:6]):[cH;D2;+0:7]:[c:8]:[c:9]-[C:10]=[O;D1;H0:11]>>[#8:4]-[c:5](:[c:6]):[c;H0;D3;+0:7](-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3]):[c:8]:[c:9]-[C:10]=[O;D1;H0:11] | null | [] | null | null | 30 | MINUTE | 38 g of 2-chloro-3-formyl-6-methoxyphenyl acetate are introduced portionwise at -5° to -10° within 15 minutes into 150 ml of 98 percent nitric acid. After stirring at -5° for 30 minutes the reaction mixture is poured into 1.5 l of ice-water and extracted three times with 500 ml of methylene chloride. The combined organ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | null | null | 0.5 | COc1ccc(C=O)c(Cl)c1OC(C)=O.O=[N+]([O-])O>>COc1c([N+](=O)[O-])cc(C=O)c(Cl)c1OC(C)=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-04542192903b4a61b15fae02838c30bf | COc1c([N+](=O)[O-])cc(C=O)c(Cl)c1OC(C)=O>>COc1c([N+](=O)[O-])cc(C=O)c(Cl)c1O | C(C)(=O)OC1=C(C(=CC(=C1OC)[N+](=O)[O-])C=O)Cl.[OH-].[Na+]>>ClC1=C(C=O)C=C(C(=C1O)OC)[N+](=O)[O-] | CC(=O)[O:15][c:14]1[c:3]([O:2][CH3:1])[c:4]([N+:5](=[O:6])[O-:7])[cH:8][c:9]([CH:10]=[O:11])[c:12]1[Cl:13]>>[CH3:1][O:2][c:3]1[c:4]([N+:5](=[O:6])[O-:7])[cH:8][c:9]([CH:10]=[O:11])[c:12]([Cl:13])[c:14]1[OH:15] | COc1c([N+](=O)[O-])cc(C=O)c(Cl)c1OC(C)=O | COc1c([N+](=O)[O-])cc(C=O)c(Cl)c1O | null | null | CO | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | db7d50f1ad65e3456617ab9bc6ab5b9ede0e069a6dd971d117a653e2a40b05de | efe1c37482b229370967d04d1a68db10ee663983a92b84fa0f009f5bb178597f | c1ccccc1 | C-C(=O)-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 1 | HOUR | 35.8 g of 2-chloro-3-formyl-6-methoxy-5-nitrophenyl acetate are dissolved in 300 ml of methanol. After adding 145 ml of 1N sodium hydroxide solution the mixture is stirred at 23° for 1 hour. After evaporation of the methanol, the residue is diluted with ice-water, made acid with 2N hydrochloric acid and extracted twice... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Aromatic alcohol | null | null | c1ccccc1 | HO- | CO | null | 1 | COc1c([N+](=O)[O-])cc(C=O)c(Cl)c1OC(C)=O>CO>COc1c([N+](=O)[O-])cc(C=O)c(Cl)c1O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-7f6cc42752fd43e580fbb39916f6c86d | COc1c([N+](=O)[O-])cc(C=O)c(Cl)c1O>>O=Cc1cc([N+](=O)[O-])c(O)c(O)c1Cl | ClC1=C(C=O)C=C(C(=C1O)OC)[N+](=O)[O-].B(Br)(Br)Br.CO>>ClC1=C(C=O)C=C(C(=C1O)O)[N+](=O)[O-] | C[O:10][c:9]1[c:5]([N+:6](=[O:7])[O-:8])[cH:4][c:3]([CH:2]=[O:1])[c:13]([Cl:14])[c:11]1[OH:12]>>[O:1]=[CH:2][c:3]1[cH:4][c:5]([N+:6](=[O:7])[O-:8])[c:9]([OH:10])[c:11]([OH:12])[c:13]1[Cl:14] | COc1c([N+](=O)[O-])cc(C=O)c(Cl)c1O | O=Cc1cc([N+](=O)[O-])c(O)c(O)c1Cl | null | null | C(Cl)Cl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccccc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 18 | HOUR | 1.3 g of 2-chloro-3-hydroxy-5-nitro-p-anisaldehyde are dissolved in 80 ml of methylene chloride, treated with 0.82 ml of boron tribromide, stirred at 23° for 18 hours, the reaction mixture is treated with 5 ml of methanol while cooling with ice, evaporated, the residue is dried in a high vacuum, digested in water, filt... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1 | Other | C(Cl)Cl | null | 18 | COc1c([N+](=O)[O-])cc(C=O)c(Cl)c1O>C(Cl)Cl>O=Cc1cc([N+](=O)[O-])c(O)c(O)c1Cl |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-347d0de9fc8f4b8ab317265c8c27e025 | COc1ccc(C=O)c(Cl)c1O.NO>>COc1ccc(C=NO)c(Cl)c1O | ClC1=C(C=O)C=CC(=C1O)OC.Cl.NO>>ClC1=C(C=NO)C=CC(=C1O)OC | O=[CH:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:12]([OH:13])[c:10]1[Cl:11].[NH2:8][OH:9]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]=[N:8][OH:9])[c:10]([Cl:11])[c:12]1[OH:13] | COc1ccc(C=O)c(Cl)c1O.NO | COc1ccc(C=NO)c(Cl)c1O | null | null | C(C)O | Heteroatom Alkylation and Arylation | OtherReaction | 26f32c058bcc6b69b34e9c38433bccb165270e0a55ab24439c783c1aee9d8dac | 3593c4a8dedbac5f92a1a749cef37ecd686935362f91b9154f0c9930a5edea38 | c1ccccc1 | O=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4].[NH2;D1;+0:5]-[O;D1;H1:6]>>[O;D1;H1:6]-[N;H0;D2;+0:5]=[CH;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | A mixture of 30 g of 2-chloro-3-hydroxy-p-anisaldehyde and 230 ml of ethanol is stirred at 70° for 4 hours in the presence of 12.3 g of hydroxylamine hydrochloride, the reaction mixture is subsequently evaporated, the residue is dried in a high vacuum and recrystallized from methanol/water. There is obtained 2-chloro-3... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Oxime | null | null | c1ccccc1 | HO- | C(C)O | null | null | COc1ccc(C=O)c(Cl)c1O.NO>C(C)O>COc1ccc(C=NO)c(Cl)c1O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-8681f9ffadc9499b94e1deba5b70ed84 | CC(=O)OC(C)=O.COc1ccc(C=NO)c(Cl)c1O>>COc1ccc(C#N)c(Cl)c1OC(C)=O | ClC1=C(C=NO)C=CC(=C1O)OC.C(C)(=O)OC(C)=O>>C(C)(=O)OC1=C(C(=CC=C1OC)C#N)Cl | CC(=O)O[C:13]([CH3:14])=[O:15].O[N:8]=[CH:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:11]([OH:12])[c:9]1[Cl:10]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]#[N:8])[c:9]([Cl:10])[c:11]1[O:12][C:13]([CH3:14])=[O:15] | CC(=O)OC(C)=O.COc1ccc(C=NO)c(Cl)c1O | COc1ccc(C#N)c(Cl)c1OC(C)=O | null | null | null | Acylation | OtherReaction | 32f0ffa82bac82cc9c70f81dd9cff4e3840e698d44934ff3b42713a8ea691cf9 | 35c5e50a61724aafba8a2be92d21ca275acb529fcfda2ff9cbf245ab9a7fbc6b | c1ccccc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].O-[N;H0;D2;+0:4]=[CH;D2;+0:5]-[c:6](:[c:7]):[c:8]:[c:9](-[OH;D1;+0:10]):[c:11]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[O;H0;D2;+0:10]-[c:9](:[c:11]):[c:8]:[c:6](-[C;H0;D2;+0:5]#[N;H0;D1;+0:4]):[c:7] | null | [] | null | null | 1 | HOUR | 21 g of 2-chloro-3-hydroxy-p-anisaldehyde oxime are heated under reflux for 20 hours together with 400 ml of acetic anhydride. Thereupon, the reaction mixture is evaporated, the residue is treated with 300 ml of ice-water, stirred for 1 hour, decanted, the thus-cooled residue is partitioned between methylene chloride a... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Aromatic alcohol.Oxime | Ester.Nitrile | null | null | c1ccccc1 | HO- | null | null | 1 | CC(=O)OC(C)=O.COc1ccc(C=NO)c(Cl)c1O>>COc1ccc(C#N)c(Cl)c1OC(C)=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-fcb953faf03c4791831ba3eeb3f3b088 | CC(=O)[O-].COc1ccc(CCl)c(F)c1OC>>COc1ccc(COC(C)=O)c(F)c1OC | ClCC1=C(C(=C(C=C1)OC)OC)F.C(C)(=O)[O-].[K+]>>C(C)(=O)OCC1=C(C(=C(C=C1)OC)OC)F | [O-:8][C:9]([CH3:10])=[O:11].Cl[CH2:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:14]([O:15][CH3:16])[c:12]1[F:13]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][O:8][C:9]([CH3:10])=[O:11])[c:12]([F:13])[c:14]1[O:15][CH3:16] | CC(=O)[O-].COc1ccc(CCl)c(F)c1OC | COc1ccc(COC(C)=O)c(F)c1OC | null | null | CN(C=O)C | Heteroatom Alkylation and Arylation | OtherReaction | c07f6f64ff82321b3607467d1ee707cb9bab7ac0cd7c3098b7f6ee7c8546417e | 670c5cfed3b5aa12e0b1c180fc6f2dc23f2114806bdb54cf3b29925a677cc9b5 | c1ccccc1 | Cl-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4].[C;D1;H3:5]-[C:6](-[O-;H0;D1:7])=[O;D1;H0:8]>>[C;D1;H3:5]-[C:6](=[O;D1;H0:8])-[O;H0;D2;+0:7]-[CH2;D2;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | 5.5 g of α-chloro-2-fluoro-3,4-dimethoxytoluene and 4.05 g of potassium acetate are stirred at 80° for 25 hours in 50 ml of dimethylformamide. The reaction mixture is subsequently poured into 150 ml of ice-water and extracted with ether. The ether phases are washed with sodium chloride solution, dried over sodium sulfa... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide | Ester | null | null | c1ccccc1 | Other | CN(C=O)C | null | null | CC(=O)[O-].COc1ccc(CCl)c(F)c1OC>CN(C=O)C>COc1ccc(COC(C)=O)c(F)c1OC |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-1909ce45d4da4c9e89f8550b972686de | COc1ccc(COC(C)=O)c(F)c1OC>>COc1ccc(CO)c(F)c1OC | C(C)(=O)OCC1=C(C(=C(C=C1)OC)OC)F.[OH-].[Na+]>>FC1=C(CO)C=CC(=C1OC)OC | CC(=O)[O:8][CH2:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:11]([O:12][CH3:13])[c:9]1[F:10]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][OH:8])[c:9]([F:10])[c:11]1[O:12][CH3:13] | COc1ccc(COC(C)=O)c(F)c1OC | COc1ccc(CO)c(F)c1OC | null | null | CO | Reduction | Hydrolysis or Hydrogenolysis of Carboxylic Esters or Thioesters | 21d61543c6ec8a8cebe1b3ef55ef3dd20acbf79a4f1c12a7fb51e32be7a3248a | 1fbcd628a0426673c5d10aa49a977cd2d1ae02a8cdf57bbb10d94aa03a94e937 | c1ccccc1 | C-C(=O)-[O;H0;D2;+0:1]-[C:2]-[c:3]>>[OH;D1;+0:1]-[C:2]-[c:3] | null | [] | null | null | null | null | 5.4 g of 2-fluoro-3,4-dimethoxybenzyl acetate are heated to 80° for 1.5 hours together with 50 ml of methanol and 50 ml of 1N sodium hydroxide solution. After evaporation of the methanol the residue is extracted with methylene chloride. The combined extracts are washed with water, dried over sodium sulfate and evaporat... | 10.6084/m9.figshare.5104873.v1 | null | Ester | Primary alcohol | null | null | c1ccccc1 | HO- | CO | null | null | COc1ccc(COC(C)=O)c(F)c1OC>CO>COc1ccc(CO)c(F)c1OC |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-115e8272e91440f7a5b6db87c567491f | COc1ccc(CO)c(F)c1OC>>COc1ccc(C=O)c(F)c1OC | FC1=C(CO)C=CC(=C1OC)OC>>FC1=C(C=O)C=CC(=C1OC)OC | [CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH2:7][OH:8])[c:9]([F:10])[c:11]1[O:12][CH3:13]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]=[O:8])[c:9]([F:10])[c:11]1[O:12][CH3:13] | COc1ccc(CO)c(F)c1OC | COc1ccc(C=O)c(F)c1OC | null | [O-2].[O-2].[Mn+4] | C1=CC=CC=C1 | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | 41bfa9deea81b465c88ad21fdfb64a2e1ba29490558cf430df132cb98b4a538b | 0a03c6724c1862e8f86d4a463afda55b8e067dc6cb42597b472eb7cabc03eda3 | c1ccccc1 | [OH;D1;+0:1]-[CH2;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[O;H0;D1;+0:1]=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | null | null | 3.0 g of 2-fluoro-3,4-dimethoxybenzyl alcohol and 5.0 g of manganese dioxide are heated under reflux for 1 hour together with 50 ml of benzene. The insoluble constituents are subsequently filtered while washing with methylene chloride. The filtrate is evaporated and the residue is recrystallized from methylene chloride... | 10.6084/m9.figshare.5104873.v1 | null | Primary alcohol | Aldehyde | null | null | c1ccccc1 | null | [O-2].[O-2].[Mn+4].C1=CC=CC=C1 | null | null | COc1ccc(CO)c(F)c1OC>[O-2].[O-2].[Mn+4].C1=CC=CC=C1>COc1ccc(C=O)c(F)c1OC |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-10c5c9c0dee84189a6ffec9f42984a0c | COc1ccc(C=O)c(F)c1OC.NO>>COc1ccc(C#N)c(F)c1OC | FC1=C(C=O)C=CC(=C1OC)OC.Cl.NO>>FC1=C(C#N)C=CC(=C1OC)OC | O=[CH:7][c:6]1[cH:5][cH:4][c:3]([O:2][CH3:1])[c:11]([O:12][CH3:13])[c:9]1[F:10].O[NH2:8]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]#[N:8])[c:9]([F:10])[c:11]1[O:12][CH3:13] | COc1ccc(C=O)c(F)c1OC.NO | COc1ccc(C#N)c(F)c1OC | null | null | C(C)O | Miscellaneous | OtherReaction | 748a00525e7f639e600a6b1229bb8ce947b6e2e96d815c0b05b54470e6cdbc2a | a27285857ea2428fb666a281ae1a2b961eec077cb33a106e48534c99bfe3d865 | c1ccccc1 | O-[NH2;D1;+0:1].O=[CH;D2;+0:2]-[c:3](:[c:4]):[c:5]>>[N;H0;D1;+0:1]#[C;H0;D2;+0:2]-[c:3](:[c:4]):[c:5] | null | [] | null | null | 2.5 | HOUR | 4.4 g of 2-fluoro-3,4-dimethoxybenzaldehyde and 1.83 g of hydroxylamine hydrochloride are heated under reflux for 5 hours together with 30 ml of ethanol. The reaction mixture is subsequently evaporated and the residue, dried in a high vacuum at 23°, is introduced into 40 ml of phosphorus oxychloride. After stirring at ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Primary amine | Nitrile | null | null | c1ccccc1 | HO- | C(C)O | null | 2.5 | COc1ccc(C=O)c(F)c1OC.NO>C(C)O>COc1ccc(C#N)c(F)c1OC |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-be5dc06117024f248d77b9e3e045177c | COc1ccc(C#N)c(F)c1OC>>COc1ccc(C#N)c(F)c1O | B(Br)(Br)Br.FC1=C(C#N)C=CC(=C1OC)OC.B(Br)(Br)Br>>FC1=C(C#N)C=CC(=C1O)OC | C[O:12][c:11]1[c:3]([O:2][CH3:1])[cH:4][cH:5][c:6]([C:7]#[N:8])[c:9]1[F:10]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]#[N:8])[c:9]([F:10])[c:11]1[OH:12] | COc1ccc(C#N)c(F)c1OC | COc1ccc(C#N)c(F)c1O | null | null | C(Cl)Cl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccccc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 1 | HOUR | 2.0 g of 2-fluoro-3,4-dimethoxybenzonitrile are dissolved in 60 ml of methylene chloride, treated with 1.1 ml of boron tribromide, stirred at 23° for 1 hour, subsequently treated with an additional 1.0 ml of boron tribromide and stirred at 23° for an additional 80 minutes. Thereupon, the reaction mixture is poured into... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1 | Other | C(Cl)Cl | null | 1 | COc1ccc(C#N)c(F)c1OC>C(Cl)Cl>COc1ccc(C#N)c(F)c1O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-002c99dcd5cd4f52936928300c2901fb | CC(=O)OC(C)=O.COc1ccc(C#N)c(F)c1O>>COc1ccc(C#N)c(F)c1OC(C)=O | FC1=C(C#N)C=CC(=C1O)OC.C(C)(=O)OC(C)=O>>C(C)(=O)OC1=C(C(=CC=C1OC)C#N)F | CC(=O)O[C:13]([CH3:14])=[O:15].[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]#[N:8])[c:9]([F:10])[c:11]1[OH:12]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([C:7]#[N:8])[c:9]([F:10])[c:11]1[O:12][C:13]([CH3:14])=[O:15] | CC(=O)OC(C)=O.COc1ccc(C#N)c(F)c1O | COc1ccc(C#N)c(F)c1OC(C)=O | null | null | N1=CC=CC=C1 | Acylation | Acetic anhydride and alcohol to ester | 55f321cc520ab80a97c517ea4db1ffe6ba0ea312e2db70f74b0966421bec0a44 | 96218bff9f96200922f4dff3481116557fe6986cba41ef7bff8cc8a0b43bd224 | c1ccccc1 | C-C(=O)-O-[C;H0;D3;+0:1](-[C;D1;H3:2])=[O;D1;H0:3].[OH;D1;+0:4]-[c:5](:[c:6]):[c:7]>>[C;D1;H3:2]-[C;H0;D3;+0:1](=[O;D1;H0:3])-[O;H0;D2;+0:4]-[c:5](:[c:6]):[c:7] | null | [] | null | null | null | null | 0.9 g of 2-fluoro-3-hydroxy-p-anisonitrile are dissolved in 10 ml of acetic anhydride and 0.5 ml of pyridine, whereupon the mixture is stirred at 120° for 2 hours. The reaction mixture is subsequently evaporated and the residue is partitioned between ice-water and methylene chloride. The organic phase is dried over sod... | 10.6084/m9.figshare.5104873.v1 | null | Anhydride.Aromatic alcohol | Ester | null | null | c1ccccc1 | HO- | N1=CC=CC=C1 | null | null | CC(=O)OC(C)=O.COc1ccc(C#N)c(F)c1O>N1=CC=CC=C1>COc1ccc(C#N)c(F)c1OC(C)=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-b8f987fdc9fe4f5a8808ad555f22f098 | COc1ccc(C#N)c(F)c1OC(C)=O.O=[N+]([O-])O>>COc1c([N+](=O)[O-])cc(C#N)c(F)c1O | C(C)(=O)OC1=C(C(=CC=C1OC)C#N)F.[N+](=O)(O)[O-]>>FC1=C(C#N)C=C(C(=C1O)OC)[N+](=O)[O-] | CC(=O)[O:15][c:14]1[c:3]([O:2][CH3:1])[cH:4][cH:8][c:9]([C:10]#[N:11])[c:12]1[F:13].O[N+:5](=[O:6])[O-:7]>>[CH3:1][O:2][c:3]1[c:4]([N+:5](=[O:6])[O-:7])[cH:8][c:9]([C:10]#[N:11])[c:12]([F:13])[c:14]1[OH:15] | COc1ccc(C#N)c(F)c1OC(C)=O.O=[N+]([O-])O | COc1c([N+](=O)[O-])cc(C#N)c(F)c1O | null | null | null | Functional Group Addition | OtherReaction | 76a9106290f5394e496e64f58cbce3a73ea6193a89aa316de0b7adb5bfa24648 | 4ffd82c1cb4692ad4f766bcb8b3f6924f10168e998e9108cc8b7fffc652667a4 | c1ccccc1 | C-C(=O)-[O;H0;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[c:5]:[cH;D2;+0:6]:[c:7]:1-[#8:8].O-[N+;H0;D3:9](-[O;-;D1;H0:10])=[O;D1;H0:11]>>[#8:8]-[c:7]1:[c:2](-[OH;D1;+0:1]):[c:3]:[c:4]:[c:5]:[c;H0;D3;+0:6]:1-[N+;H0;D3:9](-[O;-;D1;H0:10])=[O;D1;H0:11] | null | [] | null | null | 1 | HOUR | 0.8 g of 3-cyano-2-fluoro-6-methoxyphenyl acetate are introduced in three portions at -15° into 5 ml of 96 percent nitric acid, whereupon the mixture is stirred at -10° for 1 hour. Thereupon, the reaction mixture is poured on to 50 g of ice. The mixture is extracted twice with 70 ml of ethyl acetate each time. The comb... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Nitrate | Nitro group.Aromatic alcohol | c1ccccc1 | c1ccccc1 | c1ccccc1 | HO- | null | null | 1 | COc1ccc(C#N)c(F)c1OC(C)=O.O=[N+]([O-])O>>COc1c([N+](=O)[O-])cc(C#N)c(F)c1O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-abef29f5caa94a9cb778712b3fff66cd | COc1c([N+](=O)[O-])cc(C#N)c(F)c1O>>N#Cc1cc([N+](=O)[O-])c(O)c(O)c1F | C(C)O.B(Br)(Br)Br.FC1=C(C#N)C=C(C(=C1O)OC)[N+](=O)[O-].B(Br)(Br)Br>>FC1=C(C#N)C=C(C(=C1O)O)[N+](=O)[O-] | C[O:10][c:9]1[c:5]([N+:6](=[O:7])[O-:8])[cH:4][c:3]([C:2]#[N:1])[c:13]([F:14])[c:11]1[OH:12]>>[N:1]#[C:2][c:3]1[cH:4][c:5]([N+:6](=[O:7])[O-:8])[c:9]([OH:10])[c:11]([OH:12])[c:13]1[F:14] | COc1c([N+](=O)[O-])cc(C#N)c(F)c1O | N#Cc1cc([N+](=O)[O-])c(O)c(O)c1F | null | null | C(Cl)Cl | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccccc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 1.5 | HOUR | 550 mg of 2-fluoro-3-hydroxy-5-nitro-p-anisonitrile are dissolved in 30 ml of methylene chloride, whereupon the solution is treated with 0.44 ml of boron tribromide. After stirring at 23° for 6 hours an additional 0.1 ml of boron tribromide are added thereto, whereupon the mixture is stirred at 23° for an additional 1.... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1 | Other | C(Cl)Cl | null | 1.5 | COc1c([N+](=O)[O-])cc(C#N)c(F)c1O>C(Cl)Cl>N#Cc1cc([N+](=O)[O-])c(O)c(O)c1F |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-6db5ef07ddcc4a89ac71880935958d21 | COc1cc(C(=O)O)cc([N+](=O)[O-])c1OC.O=S(Cl)Cl>>COc1cc(C(=O)Cl)cc([N+](=O)[O-])c1OC | COC=1C=C(C(=O)O)C=C(C1OC)[N+](=O)[O-].S(=O)(Cl)Cl>>COC=1C=C(C(=O)Cl)C=C(C1OC)[N+](=O)[O-] | O[C:6]([c:5]1[cH:4][c:3]([O:2][CH3:1])[c:14]([O:15][CH3:16])[c:10]([N+:11](=[O:12])[O-:13])[cH:9]1)=[O:7].O=S(Cl)[Cl:8]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[Cl:8])[cH:9][c:10]([N+:11](=[O:12])[O-:13])[c:14]1[O:15][CH3:16] | COc1cc(C(=O)O)cc([N+](=O)[O-])c1OC.O=S(Cl)Cl | COc1cc(C(=O)Cl)cc([N+](=O)[O-])c1OC | null | null | null | Functional Group Interconversion | Alcohol to chloride_SOCl2 | c301c14a9dcd0670d52e8b77396cbe7fd8edeedd757bc43f4162ade1fc52fc93 | 787f545db5dc0b29dde55b5fbed7db8625b8055f49327f97ed4d83cc47c3af1d | c1ccccc1 | Cl-S(=O)-[Cl;H0;D1;+0:1].O-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6]>>[Cl;H0;D1;+0:1]-[C;H0;D3;+0:2](=[O;D1;H0:3])-[c:4](:[c:5]):[c:6] | null | [] | null | null | 1 | HOUR | 9.5 g of 3,4-dimethoxy-5-nitrobenzoic acid are suspended in 95 ml of thionyl chloride. The suspension is stirred at 80° for 1 hour. By two-fold evaporation with the addition of absolute toluene there are obtained 10 g of 3,4-dimethoxy-5-nitrobenzoyl chloride which is dissolved in 100 ml of tetrahydrofuran. This solutio... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid | Acyl halide | null | null | c1ccccc1 | HCl | null | null | 1 | COc1cc(C(=O)O)cc([N+](=O)[O-])c1OC.O=S(Cl)Cl>>COc1cc(C(=O)Cl)cc([N+](=O)[O-])c1OC |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-076c699d521b4fbe8824bba1b8af089d | COc1cc(N)cc([N+](=O)[O-])c1OC.c1ccncc1>>COc1cc(-c2ccccn2)cc([N+](=O)[O-])c1OC | N(=O)[O-].[Na+].COC=1C=C(N)C=C(C1OC)[N+](=O)[O-].N1=CC=CC=C1>>COC=1C=C(C=C(C1OC)[N+](=O)[O-])C1=NC=CC=C1 | N[c:5]1[cH:4][c:3]([O:2][CH3:1])[c:17]([O:18][CH3:19])[c:13]([N+:14](=[O:15])[O-:16])[cH:12]1.[cH:6]1[cH:7][cH:9][cH:8][cH:10][n:11]1>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][cH:8][cH:9][cH:10][n:11]2)[cH:12][c:13]([N+:14](=[O:15])[O-:16])[c:17]1[O:18][CH3:19] | COc1cc(N)cc([N+](=O)[O-])c1OC.c1ccncc1 | COc1cc(-c2ccccn2)cc([N+](=O)[O-])c1OC | null | null | Cl.O | C-C Coupling | OtherReaction | 699308a3bb55485003672e4156b650aca8061cacdc5f72f6569bc2d4532dc4b2 | b4142dbc8aebf8ea5ecf50af61f2215c729ea5a2dcf1f9e7fd52e13ad01c499d | c1ccc(-c2ccccn2)cc1 | N-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[#7;a:6]1:[cH;D2;+0:7]:[cH;D2;+0:8]:[cH;D2;+0:9]:[cH;D2;+0:10]:[cH;D2;+0:11]:1>>[c:3]:[c:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:11]1:[#7;a:6]:[cH;D2;+0:7]:[cH;D2;+0:9]:[cH;D2;+0:8]:[cH;D2;+0:10]:1):[c:4]:[c:5] | null | [] | null | null | 15 | MINUTE | 10 g of finely powdered 3,4-dimethoxy-5-nitroaniline are suspended in 15 ml of 12N hydrochloric acid and 40 ml of water, whereupon the suspension is stirring at 30° for 1 hour. Thereupon, 3.8 g of sodium nitrite dissolved in 20 ml of water are added dropwise thereto at -5° within 15 minutes. The solution is stirred at ... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccncc1 | c1ccccc1.c1ccncc1 | Other | Cl.O | null | 0.25 | COc1cc(N)cc([N+](=O)[O-])c1OC.c1ccncc1>Cl.O>COc1cc(-c2ccccn2)cc([N+](=O)[O-])c1OC |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-838bd3f68ff148658102a71548dbeabb | COc1cc(-c2ccccn2)cc([N+](=O)[O-])c1OC>>O=[N+]([O-])c1cc(-c2ccccn2)cc(O)c1O | COC=1C=C(C=C(C1OC)[N+](=O)[O-])C1=NC=CC=C1.Br>>Br.[N+](=O)([O-])C1=C(C(O)=CC(=C1)C1=NC=CC=C1)O | C[O:16][c:15]1[cH:14][c:7](-[c:8]2[cH:9][cH:10][cH:11][cH:12][n:13]2)[cH:6][c:5]([N+:3](=[O:2])[O-:4])[c:17]1[O:18]C>>[O:2]=[N+:3]([O-:4])[c:5]1[cH:6][c:7](-[c:8]2[cH:9][cH:10][cH:11][cH:12][n:13]2)[cH:14][c:15]([OH:16])[c:17]1[OH:18] | COc1cc(-c2ccccn2)cc([N+](=O)[O-])c1OC | O=[N+]([O-])c1cc(-c2ccccn2)cc(O)c1O | null | null | null | Deprotection | OtherReaction | a0f05885bbc65ae2846cad0ac34029941211b2ef3a426958b0c8aa83bb16fe86 | 9df751cd682ad9d54ed75d7313aaead6a019c5d37ede15c4672866d319b900ff | c1ccc(-c2ccccn2)cc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4](-[O;H0;D2;+0:5]-C):[c:6]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4](-[OH;D1;+0:5]):[c:6] | null | [] | null | null | 18 | HOUR | 1.5 g of 2-(3,4-dimethoxy-5-nitrophenyl)pyridine are dissolved in 30 ml of 48 percent aqueous hydrobromic acid. The reaction mixture is stirred at 100° for 16 hours and at 23° for 18 hours. The precipitate which thereby forms is filtered and recrystallized from methanol/ether. There is obtained 3-nitro-5-(2-pyridyl)pyr... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aromatic alcohol.Aromatic alcohol | null | null | c1ccccc1.c1ccncc1 | Other | null | null | 18 | COc1cc(-c2ccccn2)cc([N+](=O)[O-])c1OC>>O=[N+]([O-])c1cc(-c2ccccn2)cc(O)c1O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-c0628d01fb9744cd93ea9a7bf4bd4d9a | Brc1ccccn1.COc1cc(C=O)cc([N+](=O)[O-])c1OC>>COc1cc(C(O)c2ccccn2)cc([N+](=O)[O-])c1OC | C(CCC)[Li].BrC1=NC=CC=C1.COC=1C=C(C=O)C=C(C1OC)[N+](=O)[O-]>>COC=1C=C(C=C(C1OC)[N+](=O)[O-])C(O)C1=NC=CC=C1 | Br[c:8]1[cH:9][cH:10][cH:11][cH:12][n:13]1.[CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]=[O:7])[cH:14][c:15]([N+:16](=[O:17])[O-:18])[c:19]1[O:20][CH3:21]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]([OH:7])[c:8]2[cH:9][cH:10][cH:11][cH:12][n:13]2)[cH:14][c:15]([N+:16](=[O:17])[O-:18])[c:19]1[O:20][CH3:21] | Brc1ccccn1.COc1cc(C=O)cc([N+](=O)[O-])c1OC | COc1cc(C(O)c2ccccn2)cc([N+](=O)[O-])c1OC | null | null | O1CCCC1 | C-C Coupling | Grignard_alcohol | b19854b2eef93f01734a1ce1e1a8bde192af0da0e7ae2b2f44efcbe0d23365f0 | 1c0bd0afc1d5e370e3c8193faf738f03752295e40fa0eb99c756011e9a4be26b | c1ccc(Cc2ccccn2)cc1 | Br-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5].[O;H0;D1;+0:6]=[CH;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[OH;D1;+0:6]-[CH;D3;+0:7](-[c:8](:[c:9]):[c:10])-[c;H0;D3;+0:1](:[#7;a:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | 30 | MINUTE | 2.76 ml of 2-bromopyridine dissolved in 30 ml of absolute tetrahydrofuran are treated -60° within 30 minutes with 19.2 ml of 1.6M n-butyl lithium solution (in hexane), whereupon the mixture is stirred at -60° for 30 minutes. 6.0 g of 3,4-dimethoxy-5-nitrobenzaldehyde dissolved in 50 ml of tetrahydrofuran are then added... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aldehyde | Secondary alcohol | c1ccncc1 | c1ccncc1 | c1ccccc1.c1ccncc1 | Br- | O1CCCC1 | null | 0.5 | Brc1ccccn1.COc1cc(C=O)cc([N+](=O)[O-])c1OC>O1CCCC1>COc1cc(C(O)c2ccccn2)cc([N+](=O)[O-])c1OC |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-138571790bae4b9aa8198da6b9657a45 | COc1cc(C(O)c2ccccn2)cc([N+](=O)[O-])c1OC>>COc1cc(C(=O)c2ccccn2)cc([N+](=O)[O-])c1OC | COC=1C=C(C=C(C1OC)[N+](=O)[O-])C(O)C1=NC=CC=C1>>N1=C(C=CC=C1)C(=O)C1=CC(=C(C(=C1)[N+](=O)[O-])OC)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]([OH:7])[c:8]2[cH:9][cH:10][cH:11][cH:12][n:13]2)[cH:14][c:15]([N+:16](=[O:17])[O-:18])[c:19]1[O:20][CH3:21]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[c:8]2[cH:9][cH:10][cH:11][cH:12][n:13]2)[cH:14][c:15]([N+:16](=[O:17])[O-:18])[c:19]1[O:20][CH3:21] | COc1cc(C(O)c2ccccn2)cc([N+](=O)[O-])c1OC | COc1cc(C(=O)c2ccccn2)cc([N+](=O)[O-])c1OC | null | [O-2].[O-2].[Mn+4] | CC(=O)C | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | c7c20d2959ac48847b03cc1265962cf99a8ec8a85900c087dabb30077298c66c | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | O=C(c1ccccc1)c1ccccn1 | [OH;D1;+0:1]-[CH;D3;+0:2](-[c:3](:[c:4]):[c:5])-[c:6](:[c:7]):[#7;a:8]:[c:9]>>[O;H0;D1;+0:1]=[C;H0;D3;+0:2](-[c:3](:[c:4]):[c:5])-[c:6](:[c:7]):[#7;a:8]:[c:9] | null | [] | null | null | null | null | 7 g of manganese dioxide and added portionwise to 4.0 g of α-(3,4-dimethoxy-5-nitrophenyl)-2-pyridine-methanol dissolved in 100 ml of acetone while constantly heating under reflux over a period of 2.5 hours. Thereupon, the mixture is heated under reflux for an additional 2 hours. The manganese salts are subsequently fi... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | null | null | c1ccccc1.c1ccncc1 | null | [O-2].[O-2].[Mn+4].CC(=O)C | null | null | COc1cc(C(O)c2ccccn2)cc([N+](=O)[O-])c1OC>[O-2].[O-2].[Mn+4].CC(=O)C>COc1cc(C(=O)c2ccccn2)cc([N+](=O)[O-])c1OC |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-72d431bc31664859896cbd54829bb6ab | COc1cc(C(C)=O)cc([N+](=O)[O-])c1OC>>COc1cc(C(C)=O)cc(N)c1OC | C(O)([O-])=O.[Na+].C(Cl)Cl.O.O.[Sn](Cl)Cl.COC=1C=C(C=C(C1OC)[N+](=O)[O-])C(C)=O>>NC=1C(=C(C=C(C1)C(C)=O)OC)OC | O=[N+:11]([O-])[c:10]1[cH:9][c:5]([C:6]([CH3:7])=[O:8])[cH:4][c:3]([O:2][CH3:1])[c:12]1[O:13][CH3:14]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6]([CH3:7])=[O:8])[cH:9][c:10]([NH2:11])[c:12]1[O:13][CH3:14] | COc1cc(C(C)=O)cc([N+](=O)[O-])c1OC | COc1cc(C(C)=O)cc(N)c1OC | null | null | C(C)O | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 30 | MINUTE | 11.3 g of tin dichloride dihydrate are added to 2.25 g of 3',4'-dimethoxy-5'-nitroacetophenone dissolved in 50 ml of ethanol, where upon the mixture is stirred at 75° for 30 minutes. Thereupon, the reaction mixture is poured on to 100 g of ice, neutralized with about 300 ml of saturated sodium hydrogen carbonate soluti... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1 | Other | C(C)O | null | 0.5 | COc1cc(C(C)=O)cc([N+](=O)[O-])c1OC>C(C)O>COc1cc(C(C)=O)cc(N)c1OC |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-1d614496fe8746eaa68466ab7c4f69d3 | COc1cc(C(C)=O)cc(N)c1OC>>COc1cc(C(C)=O)cc(C#N)c1OC | N(=O)[O-].[Na+].NC=1C(=C(C=C(C1)C(C)=O)OC)OC.[Cu]C#N.[C-]#N.[K+]>>C(#N)C=1C(=C(C=C(C1)C(C)=O)OC)OC | N[c:10]1[cH:9][c:5]([C:6]([CH3:7])=[O:8])[cH:4][c:3]([O:2][CH3:1])[c:13]1[O:14][CH3:15]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6]([CH3:7])=[O:8])[cH:9][c:10]([C:11]#[N:12])[c:13]1[O:14][CH3:15] | COc1cc(C(C)=O)cc(N)c1OC | COc1cc(C(C)=O)cc(C#N)c1OC | null | null | Cl.O.C(Cl)Cl | Miscellaneous | OtherReaction | 803ab123dd5297cb23d9a6340952837f436e629c02fa01486d208bb7e2b4e208 | fb780e6912aa057969f5ca1e3a4b096c038904d81ac37783ac8b177057c79824 | c1ccccc1 | N-[c;H0;D3;+0:1](:[c:2]:[c:3]-[C:4](-[C;D1;H3:5])=[O;D1;H0:6]):[c:7](-[#8:8]):[c:9]>>[#8:8]-[c:7](:[c:9]):[c;H0;D3;+0:1](-[C:10]#[N;D1;H0:11]):[c:2]:[c:3]-[C:4](-[C;D1;H3:5])=[O;D1;H0:6] | null | [] | null | null | 3 | HOUR | A solution of 5.2 g of sodium nitrite in 20 ml of water is added dropwise at 0° within 20 minutes to 14.0 g of 5'-amino-3',4'-dimethoxyacetophenone dissolved in 155 ml of 1N hydrochloric acid. After stirring at -2° for 30 minutes the cold diazonium salt solution is added dropwise within 30 minutes at 5°-10° to a soluti... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | Nitrile | c1ccccc1 | c1ccccc1 | c1ccccc1 | null | Cl.O.C(Cl)Cl | null | 3 | COc1cc(C(C)=O)cc(N)c1OC>Cl.O.C(Cl)Cl>COc1cc(C(C)=O)cc(C#N)c1OC |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-b79afe6cf01145269c98968a6f2b63e0 | CC(=O)Oc1cc(C(C)=O)cc(C#N)c1OC(C)=O>>CC(=O)c1cc(O)c(O)c(C#N)c1 | C(#N)C=1C(=C(C=C(C1)C(C)=O)OC(C)=O)OC(C)=O.[OH-].[Na+].Cl>>C(#N)C=1C(=C(C=C(C1)C(C)=O)O)O | CC(=O)[O:7][c:6]1[cH:5][c:4]([C:2]([CH3:1])=[O:3])[cH:13][c:10]([C:11]#[N:12])[c:8]1[O:9]C(C)=O>>[CH3:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([OH:7])[c:8]([OH:9])[c:10]([C:11]#[N:12])[cH:13]1 | CC(=O)Oc1cc(C(C)=O)cc(C#N)c1OC(C)=O | CC(=O)c1cc(O)c(O)c(C#N)c1 | null | null | [Cl-].[Na+].CO | Reduction | OtherReaction | 7b7e32f38c8a719ca98099bc0a6aa138d56231b7b04ad475d74b1a13991ac98f | e01d5791a75e3a08093f57d62c9c2d4bec3d7dc239371b69a4320a81141226de | c1ccccc1 | C-C(=O)-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4](-[O;H0;D2;+0:5]-C(-C)=O):[c:6]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4](-[OH;D1;+0:5]):[c:6] | null | [] | null | null | 45 | MINUTE | 0.33 g of 5'-cyano-3',4'-diacetoxyacetophenone dissolved in 3.3 ml of methanol is treated with 2.7 ml of 1.0N sodium hydroxide solution and the reaction mixture is stirred at 23° for 45 minutes. The mixture is subsequently acidified with 2N hydrochloric acid, diluted with 5 ml of saturated sodium chloride solution and ... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ester | Aromatic alcohol.Aromatic alcohol | null | null | c1ccccc1 | HO- | [Cl-].[Na+].CO | null | 0.75 | CC(=O)Oc1cc(C(C)=O)cc(C#N)c1OC(C)=O>[Cl-].[Na+].CO>CC(=O)c1cc(O)c(O)c(C#N)c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-c78ed60ce4d4418a8dcb40009c1e999f | COc1cc(C(C)=O)cc(C#N)c1OC.[Br-]>>COc1cc(C(=O)CBr)cc(C#N)c1OC | [Br-].[Br-].[Br-].C1(=CC=CC=C1)[N+](C)(C)C.C1(=CC=CC=C1)[N+](C)(C)C.C1(=CC=CC=C1)[N+](C)(C)C.C(#N)C=1C(=C(C=C(C1)C(C)=O)OC)OC>>BrCC(=O)C=1C=C(C(=C(C#N)C1)OC)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[CH3:8])[cH:10][c:11]([C:12]#[N:13])[c:14]1[O:15][CH3:16].[Br-:9]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[CH2:8][Br:9])[cH:10][c:11]([C:12]#[N:13])[c:14]1[O:15][CH3:16] | COc1cc(C(C)=O)cc(C#N)c1OC.[Br-] | COc1cc(C(=O)CBr)cc(C#N)c1OC | null | null | O1CCCC1 | Functional Group Interconversion | Bromination | 97ca6720945af5a02c450d33ec56e946521050f9771c27f9cfcb85f3477593f6 | cb3e14519230141aa015a4cf9c960def3e60f01997e61621f62506924bfa15de | c1ccccc1 | [Br-;H0;D0:1].[CH3;D1;+0:2]-[C:3](=[O;D1;H0:4])-[c:5]>>[Br;H0;D1;+0:1]-[CH2;D2;+0:2]-[C:3](=[O;D1;H0:4])-[c:5] | null | [] | null | null | 30 | MINUTE | 3.48 g of phenyltrimethylammonium bromide dibromide dissolved in 30 ml of tetrahydrofuran are added dropwise at room temperature within 45 minutes to 1.9 g of 5'-cyano-3',4'-dimethoxyacetophenone dissolved in 30 ml of tetrahydrofuran, whereupon the mixture is stirred for 30 minutes. Thereupon, the reaction mixture is p... | 10.6084/m9.figshare.5104873.v1 | null | Ketone | Primary halide | null | null | c1ccccc1 | null | O1CCCC1 | null | 0.5 | COc1cc(C(C)=O)cc(C#N)c1OC.[Br-]>O1CCCC1>COc1cc(C(=O)CBr)cc(C#N)c1OC |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-f6977aa0d80c429f9df66a31c9bc9ed9 | CCCCCCO.COc1cc(C(=O)CBr)cc(C#N)c1OC>>CCCCCCOC(=O)C(=O)c1cc(C#N)c(OC)c(OC)c1 | BrCC(=O)C=1C=C(C(=C(C#N)C1)OC)OC.[Se](=O)=O.C(CCCCC)O>>C(#N)C=1C=C(C=C(C1OC)OC)C(C(=O)OCCCCCC)=O | [CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][OH:7].Br[CH2:8][C:10](=[O:11])[c:12]1[cH:13][c:14]([C:15]#[N:16])[c:17]([O:18][CH3:19])[c:20]([O:21][CH3:22])[cH:23]1>>[CH3:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8](=[O:9])[C:10](=[O:11])[c:12]1[cH:13][c:14]([C:15]#[N:16])[c:17]([O:18][CH3:19])[c:20]([O:21][CH3:22])[cH:... | CCCCCCO.COc1cc(C(=O)CBr)cc(C#N)c1OC | CCCCCCOC(=O)C(=O)c1cc(C#N)c(OC)c(OC)c1 | null | null | C(Cl)Cl | Acylation | OtherReaction | fd2eb18b6571f5871d34af3ee3047ac4a3cf01c29ff7067109d016d3324c22a1 | 6a9d9df581b58124b36acc38fbe3ba14c5c991095298763ede7bc1de3bebb9ed | c1ccccc1 | Br-[CH2;D2;+0:1]-[C:2](=[O;D1;H0:3])-[c:4].[C:5]-[C:6]-[OH;D1;+0:7]>>[C:5]-[C:6]-[O;H0;D2;+0:7]-[C;H0;D3;+0:1](=[O;D1;H0:8])-[C:2](=[O;D1;H0:3])-[c:4] | null | [] | null | null | null | null | 1.45 g of 5-(bromoacetyl)-2,3-dimethoxybenzonitrile and 1.12 g of selenium dioxide are stirred at 120° for 18 hours in 10 ml of n-hexanol. After cooling to room temperature the mixture is diluted with 20 ml of methylene chloride and filtered. The filtrate is washed with water, dried over sodium sulfate and evaporated. ... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Ketone.Primary alcohol | Ketone.Ester | null | null | c1ccccc1 | null | C(Cl)Cl | null | null | CCCCCCO.COc1cc(C(=O)CBr)cc(C#N)c1OC>C(Cl)Cl>CCCCCCOC(=O)C(=O)c1cc(C#N)c(OC)c(OC)c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-d4c019c0ee504fbcb26b1a4e1bbfb723 | CCCCCCOC(=O)C(=O)c1cc(C#N)c(OC)c(OC)c1.CO>>COC(=O)C(=O)c1cc(O)c(O)c(C#N)c1 | B(Br)(Br)Br.C(#N)C=1C=C(C=C(C1OC)OC)C(C(=O)OCCCCCC)=O.CO>>C(#N)C=1C=C(C=C(C1O)O)C(C(=O)OC)=O | CCCCCCO[C:3](=[O:4])[C:5](=[O:6])[c:7]1[cH:8][c:9]([O:10]C)[c:11]([O:12]C)[c:13]([C:14]#[N:15])[cH:16]1.[CH3:1][OH:2]>>[CH3:1][O:2][C:3](=[O:4])[C:5](=[O:6])[c:7]1[cH:8][c:9]([OH:10])[c:11]([OH:12])[c:13]([C:14]#[N:15])[cH:16]1 | CCCCCCOC(=O)C(=O)c1cc(C#N)c(OC)c(OC)c1.CO | COC(=O)C(=O)c1cc(O)c(O)c(C#N)c1 | null | null | C(Cl)Cl | Acylation | OtherReaction | 45b76bc55158a7fdc76d615b88975278da28f9f255a75a92ab6cf29195d4bd68 | ce7f59759ec537efe3edc3c1438a9c101c515dfb02fdc01bd53c5cf859cd614c | c1ccccc1 | C-C-C-C-C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](=[O;D1;H0:4])-[c:5]:[c:6]:[c:7](-[O;H0;D2;+0:8]-C):[c:9](-[O;H0;D2;+0:10]-C):[c:11].[C;D1;H3:12]-[OH;D1;+0:13]>>[C;D1;H3:12]-[O;H0;D2;+0:13]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3](=[O;D1;H0:4])-[c:5]:[c:6]:[c:7](-[OH;D1;+0:8]):[c:9](-[OH;D1;+0:10]):[c:11] | null | [] | null | null | 18 | HOUR | 4.8 ml of boron tribromide dissolved in 20 ml of methylene chloride are added dropwise while cooling with ice within 20 minutes to 4.0 g of hexyl (3-cyano-4,5-dimethoxyphenyl)glyoxylate dissolved in 100 ml of methylene chloride and the reaction mixture is stirred at room temperature for 18 hours. 40 ml of methanol are ... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Ether.Ether.Methanol | Ketone.Ester.Aromatic alcohol.Aromatic alcohol | null | null | c1ccccc1 | HO- | C(Cl)Cl | null | 18 | CCCCCCOC(=O)C(=O)c1cc(C#N)c(OC)c(OC)c1.CO>C(Cl)Cl>COC(=O)C(=O)c1cc(O)c(O)c(C#N)c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-0548a9daa64744ec8755fee0bf4c32c0 | COC(=O)C(=O)c1cc(O)c(O)c(C#N)c1.Cc1ccc(O)c(N)c1>>Cc1ccc2oc(=O)c(-c3cc(O)c(O)c(C#N)c3)nc2c1 | C(#N)C=1C=C(C=C(C1O)O)C(C(=O)OC)=O.NC1=CC(=CC=C1O)C>>OC1=C(C#N)C=C(C=C1O)C=1C(OC2=C(N1)C=C(C=C2)C)=O | CO[C:7](=[O:8])[C:9](=O)[c:10]1[cH:11][c:12]([OH:13])[c:14]([OH:15])[c:16]([C:17]#[N:18])[cH:19]1.[CH3:1][c:2]1[cH:3][cH:4][c:5]([OH:6])[c:21]([NH2:20])[cH:22]1>>[CH3:1][c:2]1[cH:3][cH:4][c:5]2[o:6][c:7](=[O:8])[c:9](-[c:10]3[cH:11][c:12]([OH:13])[c:14]([OH:15])[c:16]([C:17]#[N:18])[cH:19]3)[n:20][c:21]2[cH:22]1 | COC(=O)C(=O)c1cc(O)c(O)c(C#N)c1.Cc1ccc(O)c(N)c1 | Cc1ccc2oc(=O)c(-c3cc(O)c(O)c(C#N)c3)nc2c1 | null | null | O.CN(C=O)C | Aromatic Heterocycle Formation | OtherReaction | fd4f5a2c5cd75f09b9ffd249cd94a3df5f247480207d1a3b18feea871eb5b7e8 | c7371540e6bbfa0cc65c0d222916a85bfb12611676b69973853bf515c0385853 | O=c1oc2ccccc2nc1-c1ccccc1 | C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C;H0;D3;+0:3](=O)-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8].[NH2;D1;+0:9]-[c:10](:[c:11]):[c:12](-[OH;D1;+0:13]):[c:14]>>[O;D1;H0:2]=[c;H0;D3;+0:1]1:[o;H0;D2;+0:13]:[c:12](:[c:14]):[c:10](:[c:11]):[n;H0;D2;+0:9]:[c;H0;D3;+0:3]:1-[c;H0;D3;+0:4](:[c:5]:[c:6]):[c:7]:[c:8] | null | [] | null | null | null | null | 1.075 g of methyl (3-cyano-4,5-dihydroxyphenyl)glyoxylate and 0.60 g of 2-amino-p-cresol are stirred at 120° for 70 minutes in 2 ml of dimethylformamide. The mixture is subsequently cooled to room temperature and diluted with 15 ml of water: The precipitate is filtered and dried in a water-jet vacuum at 80° for 6 hours... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Aromatic alcohol.Primary amine | null | c1ccccc1 | c1ccc2occnc2c1 | c1ccc2occnc2c1.c1ccccc1 | HO- | O.CN(C=O)C | null | null | COC(=O)C(=O)c1cc(O)c(O)c(C#N)c1.Cc1ccc(O)c(N)c1>O.CN(C=O)C>Cc1ccc2oc(=O)c(-c3cc(O)c(O)c(C#N)c3)nc2c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-eb6ade9b578e419f95798fbe9a0df127 | COc1cc(C(=O)Cl)cc([N+](=O)[O-])c1OC.[C-]#[N+]CC(=O)OCC>>CCOC(=O)c1ncoc1-c1cc(OC)c(OC)c([N+](=O)[O-])c1 | COC=1C=C(C(=O)Cl)C=C(C1OC)[N+](=O)[O-].[N+](#[C-])CC(=O)OCC.C(C)N(CC)CC>>COC=1C=C(C=C(C1OC)[N+](=O)[O-])C1=C(N=CO1)C(=O)OCC | Cl[C:10](=[O:9])[c:11]1[cH:12][c:13]([O:14][CH3:15])[c:16]([O:17][CH3:18])[c:19]([N+:20](=[O:21])[O-:22])[cH:23]1.[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][N+:7]#[C-:8]>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[c:6]1[n:7][cH:8][o:9][c:10]1-[c:11]1[cH:12][c:13]([O:14][CH3:15])[c:16]([O:17][CH3:18])[c:19]([N+:20](=[O:21])[O-:22])[... | COc1cc(C(=O)Cl)cc([N+](=O)[O-])c1OC.[C-]#[N+]CC(=O)OCC | CCOC(=O)c1ncoc1-c1cc(OC)c(OC)c([N+](=O)[O-])c1 | null | null | O1CCCC1 | Aromatic Heterocycle Formation | OtherReaction | e0691b0e647d306cbec2c633b812f4016dd56910f99a49385ec7320bbb557520 | b41ec8a08aa491bfeb3f8ab13e61b9529bee47477ae112dede5847f1b44831e2 | c1ccc(-c2cnco2)cc1 | Cl-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7].[C-;H0;D1:8]#[N+;H0;D2:9]-[CH2;D2;+0:10]-[C:11](=[O;D1;H0:12])-[#8:13]-[C:14]>>[C:14]-[#8:13]-[C:11](=[O;D1;H0:12])-[c;H0;D3;+0:10]1:[n;H0;D2;+0:9]:[cH;D2;+0:8]:[o;H0;D2;+0:2]:[c;H0;D3;+0:1]:1-[c;H0;D3;+0:3](:[c:4]:[c:5]):[c:6]:[c:7] | null | [] | null | null | 48 | HOUR | A solution of 2.5 g of 3,4-dimethoxy-5-nitrobenzoyl chloride in 10 ml of absolute tetrahydrofuran is treated with 1.1 ml of ethyl isocyanoacetate and subsequently with a solution of 3.0 ml of triethylamine in 10 ml of tetrahydrofuran and stirred at room temperature for 48 hours. After distillation of the solvent, the r... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ester.Isocyanide | Ester | null | c1cocn1 | c1cocn1.c1ccccc1 | HCl | O1CCCC1 | null | 48 | COc1cc(C(=O)Cl)cc([N+](=O)[O-])c1OC.[C-]#[N+]CC(=O)OCC>O1CCCC1>CCOC(=O)c1ncoc1-c1cc(OC)c(OC)c([N+](=O)[O-])c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-b8fb12249774430bae0b862b8d550c7a | CCOC(=O)c1ncoc1-c1cc(OC)c(OC)c([N+](=O)[O-])c1>>NCC(=O)c1cc(O)c(O)c([N+](=O)[O-])c1 | COC=1C=C(C=C(C1OC)[N+](=O)[O-])C1=C(N=CO1)C(=O)OCC.Br>>Br.NCC(=O)C1=CC(=C(C(=C1)[N+](=O)[O-])O)O | CCOC(=O)[c:3]1[n:2]c[o:5][c:4]1-[c:6]1[cH:7][c:8]([O:9]C)[c:10]([O:11]C)[c:12]([N+:13](=[O:14])[O-:15])[cH:16]1>>[NH2:2][CH2:3][C:4](=[O:5])[c:6]1[cH:7][c:8]([OH:9])[c:10]([OH:11])[c:12]([N+:13](=[O:14])[O-:15])[cH:16]1 | CCOC(=O)c1ncoc1-c1cc(OC)c(OC)c([N+](=O)[O-])c1 | NCC(=O)c1cc(O)c(O)c([N+](=O)[O-])c1 | null | null | null | Reduction | OtherReaction | 8426a7f6c200afe48c14003c6f896bd2e560e475a0ae2af0597a3400c6c5e0a4 | aef5864b38f340a76c86895e7c33929cfb27e246092acfe05a6dec048cfc09a0 | c1ccccc1 | C-C-O-C(=O)-[c;H0;D3;+0:1]1:[n;H0;D2;+0:2]:c:[o;H0;D2;+0:3]:[c;H0;D3;+0:4]:1-[c;H0;D3;+0:5]1:[c:6]:[c:7]:[c:8](-[O;H0;D2;+0:9]-C):[c:10](-[O;H0;D2;+0:11]-C):[c:12]:1>>[NH2;D1;+0:2]-[CH2;D2;+0:1]-[C;H0;D3;+0:4](=[O;H0;D1;+0:3])-[c;H0;D3;+0:5]1:[c:6]:[c:7]:[c:8](-[OH;D1;+0:9]):[c:10](-[OH;D1;+0:11]):[c:12]:1 | null | [] | null | null | 2 | HOUR | 1.0 g of ethyl 5-(3,4-dimethoxy-5-nitrophenyl)-4-oxazolecarboxylate is treated with 10 ml of constant-boiling hydrobromic acid and stirred at 140° for 2 hours. After distillation of the excess hydrobromic acid, the yellow residue is recrystallized from ethanol/acetone. There is obtained 2-amino-3',4'-dihydroxy-5'-nitro... | 10.6084/m9.figshare.5104873.v1 | null | Ester.Ether.Ether | Ketone.Aromatic alcohol.Aromatic alcohol.Primary amine | c1cocn1 | null | c1ccccc1 | HO- | null | null | 2 | CCOC(=O)c1ncoc1-c1cc(OC)c(OC)c([N+](=O)[O-])c1>>NCC(=O)c1cc(O)c(O)c([N+](=O)[O-])c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-1a00a79d21e04becbe2fce0d55438577 | CCOC(=O)CC(=O)c1cc(OC)c(OC)c([N+](=O)[O-])c1.CNN>>COc1cc(-c2cc(O)n(C)n2)cc([N+](=O)[O-])c1OC | COC=1C=C(C(=O)CC(=O)OCC)C=C(C1OC)[N+](=O)[O-].CNN>>COC=1C=C(C=C(C1OC)[N+](=O)[O-])C1=NN(C(=C1)O)C | CCO[C:8]([CH2:7][C:6](=O)[c:5]1[cH:4][c:3]([O:2][CH3:1])[c:18]([O:19][CH3:20])[c:14]([N+:15](=[O:16])[O-:17])[cH:13]1)=[O:9].[NH:10]([CH3:11])[NH2:12]>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][c:8]([OH:9])[n:10]([CH3:11])[n:12]2)[cH:13][c:14]([N+:15](=[O:16])[O-:17])[c:18]1[O:19][CH3:20] | CCOC(=O)CC(=O)c1cc(OC)c(OC)c([N+](=O)[O-])c1.CNN | COc1cc(-c2cc(O)n(C)n2)cc([N+](=O)[O-])c1OC | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | 8d693830ec5d67c6ef89694e04e2793d60b501ccd64442c2bd507d968f7b81a2 | 0296f8f78a543918519351bd347834699f291cf4e6c7e504eef51f4e914155a4 | c1ccc(-c2cc[nH]n2)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[CH2;D2;+0:3]-[C;H0;D3;+0:4](=O)-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:8]:[c:9].[C;D1;H3:10]-[NH;D2;+0:11]-[NH2;D1;+0:12]>>[C;D1;H3:10]-[n;H0;D3;+0:11]1:[n;H0;D2;+0:12]:[c;H0;D3;+0:4](-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:8]:[c:9]):[cH;D2;+0:3]:[c;H0;D3;+0:1]:1-[OH;D1;+0:2] | null | [] | null | null | null | null | 10 g of ethyl (3,4-dimethoxy-5-nitrobenzoyl)acetate are suspended in 100 ml of ethanol, treated with 1.7 g of methylhydrazine and heated under reflux for 16 hours. After distillation of about 50 ml of ethanol, the mixture is cooled to 0° and the separated precipitate is filtered under suction. After recrystallization f... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Ester | Aromatic alcohol | null | c1cc[nH]n1 | c1ccccc1.c1cc[nH]n1 | HO- | C(C)O | null | null | CCOC(=O)CC(=O)c1cc(OC)c(OC)c([N+](=O)[O-])c1.CNN>C(C)O>COc1cc(-c2cc(O)n(C)n2)cc([N+](=O)[O-])c1OC |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ebc2fd0e16614fd493f12871185908b8 | BrB(Br)Br.COc1cc(-c2cc(O)n(C)n2)cc([N+](=O)[O-])c1OC>>Br.Cn1nc(-c2cc(O)c(O)c([N+](=O)[O-])c2)cc1O | COC=1C=C(C=C(C1OC)[N+](=O)[O-])C1=NN(C(=C1)O)C.B(Br)(Br)Br.C(C)O>>Br.OC1=CC(=NN1C)C1=CC(=C(C(O)=C1)O)[N+](=O)[O-] | BrB(Br)[Br:1].C[O:9][c:8]1[cH:7][c:6](-[c:5]2[n:4][n:3]([CH3:2])[c:18]([OH:19])[cH:17]2)[cH:16][c:12]([N+:13](=[O:14])[O-:15])[c:10]1[O:11]C>>[BrH:1].[CH3:2][n:3]1[n:4][c:5](-[c:6]2[cH:7][c:8]([OH:9])[c:10]([OH:11])[c:12]([N+:13](=[O:14])[O-:15])[cH:16]2)[cH:17][c:18]1[OH:19] | BrB(Br)Br.COc1cc(-c2cc(O)n(C)n2)cc([N+](=O)[O-])c1OC | Br.Cn1nc(-c2cc(O)c(O)c([N+](=O)[O-])c2)cc1O | null | null | C(Cl)Cl | Miscellaneous | OtherReaction | 0096c728c44c2a8bd0295be3d63d1c54f13da4b5d2d19aa346c5c00964587678 | 736e5be0c4313f69ce19fa28727a9da18e7a37db0f912ae36fd9ca7a66469bc3 | c1ccc(-c2cc[nH]n2)cc1 | Br-B(-Br)-[Br;H0;D1;+0:1].C-[O;H0;D2;+0:2]-[c:3](:[c:4]):[c:5](-[O;H0;D2;+0:6]-C):[c:7]>>[BrH;D0;+0:1].[OH;D1;+0:2]-[c:3](:[c:4]):[c:5](-[OH;D1;+0:6]):[c:7] | null | [] | null | null | 1 | HOUR | 2.0 g of 3-(3,4-dimethoxy-5-nitrophenyl)-1-methylpyrazol-5-ol are suspended in 100 ml of methylene chloride. After cooling to -40° a solution of 4.9 ml of boron tribromide in 60 ml of methylene chloride is added dropwise thereto within 1 hour. The mixture is subsequently stirred at room temperature for 16 hours, cooled... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aromatic alcohol.Aromatic alcohol | null | null | c1cc[nH]n1.c1ccccc1 | HBr.B | C(Cl)Cl | null | 1 | BrB(Br)Br.COc1cc(-c2cc(O)n(C)n2)cc([N+](=O)[O-])c1OC>C(Cl)Cl>Br.Cn1nc(-c2cc(O)c(O)c([N+](=O)[O-])c2)cc1O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-9913918bbe9e496484cda70119ac0bc8 | CCOC(=O)CC(=O)c1cc(OC)c(OC)c([N+](=O)[O-])c1.NNc1ccccc1>>COc1cc(C2=NN(c3ccccc3)C(=O)C2)cc([N+](=O)[O-])c1OC | COC=1C=C(C(=O)CC(=O)OCC)C=C(C1OC)[N+](=O)[O-].C1(=CC=CC=C1)NN>>COC=1C=C(C=C(C1OC)[N+](=O)[O-])C1=NN(C(C1)=O)C1=CC=CC=C1 | CCO[C:15](=[O:16])[CH2:17][C:6](=O)[c:5]1[cH:4][c:3]([O:2][CH3:1])[c:23]([O:24][CH3:25])[c:19]([N+:20](=[O:21])[O-:22])[cH:18]1.[NH2:7][NH:8][c:9]1[cH:10][cH:11][cH:12][cH:13][cH:14]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6]2=[N:7][N:8]([c:9]3[cH:10][cH:11][cH:12][cH:13][cH:14]3)[C:15](=[O:16])[CH2:17]2)[cH:18][c:19]([N+:2... | CCOC(=O)CC(=O)c1cc(OC)c(OC)c([N+](=O)[O-])c1.NNc1ccccc1 | COc1cc(C2=NN(c3ccccc3)C(=O)C2)cc([N+](=O)[O-])c1OC | null | null | null | Acylation | OtherReaction | 2f4644354b6c5f4241ddd87aba82d68d68e6920234fa3da3de3ca1c4ec817843 | 77a4474ae747e91f24b3228e85a2d4f1b6f12a541e0621f2a2f03a59600a687c | O=C1CC(c2ccccc2)=NN1c1ccccc1 | C-C-O-[C;H0;D3;+0:1](=[O;D1;H0:2])-[C:3]-[C;H0;D3;+0:4](=O)-[c:5](:[c:6]):[c:7].[NH2;D1;+0:8]-[NH;D2;+0:9]-[c:10](:[c:11]):[c:12]>>[O;D1;H0:2]=[C;H0;D3;+0:1]1-[C:3]-[C;H0;D3;+0:4](-[c:5](:[c:6]):[c:7])=[N;H0;D2;+0:8]-[N;H0;D3;+0:9]-1-[c:10](:[c:11]):[c:12] | null | [] | null | null | null | null | 10.0 g of ethyl (3,4-dimethoxy-5-nitrobenzoyl)acetate are reacted with 4.0 g of phenylhydrazine in analogy to Example 53a. After recrystallization from methylene chloride/ethanol, there is obtained 3-(3,4-dimethoxy-5-nitrophenyl)-1-phenyl-2-pyrazolin-5-one in the form of yellow crystals of m.p. 190°-192°.
Conditions: S... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Ester | Hydrazone amide | null | C1=N[NH]CC1 | c1ccccc1.C1=N[NH]CC1.c1ccccc1 | HO- | null | null | null | CCOC(=O)CC(=O)c1cc(OC)c(OC)c([N+](=O)[O-])c1.NNc1ccccc1>>COc1cc(C2=NN(c3ccccc3)C(=O)C2)cc([N+](=O)[O-])c1OC |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-fc87f8b75e7c42279476226902a4ff53 | CCOC(=O)C(C(=O)OCC)C(=O)c1cc(OC)c(OC)c([N+](=O)[O-])c1>>CCOC(=O)CC(=O)c1cc(O)c(O)c([N+](=O)[O-])c1 | COC=1C=C(C(=O)C(C(=O)OCC)C(=O)OCC)C=C(C1OC)[N+](=O)[O-].B(Br)(Br)Br.C(C)O>>OC=1C=C(C(=O)CC(=O)OCC)C=C(C1O)[N+](=O)[O-] | CCOC(=O)[CH:6]([C:4]([O:3][CH2:2][CH3:1])=[O:5])[C:7](=[O:8])[c:9]1[cH:10][c:11]([O:12]C)[c:13]([O:14]C)[c:15]([N+:16](=[O:17])[O-:18])[cH:19]1>>[CH3:1][CH2:2][O:3][C:4](=[O:5])[CH2:6][C:7](=[O:8])[c:9]1[cH:10][c:11]([OH:12])[c:13]([OH:14])[c:15]([N+:16](=[O:17])[O-:18])[cH:19]1 | CCOC(=O)C(C(=O)OCC)C(=O)c1cc(OC)c(OC)c([N+](=O)[O-])c1 | CCOC(=O)CC(=O)c1cc(O)c(O)c([N+](=O)[O-])c1 | null | null | C(Cl)Cl | Reduction | OtherReaction | e4edf29bc7902ee5be5c22d6af37d389a593c072c5af2eba68ff2929237c4171 | b62bbe0f1dc80f5ef31c5e64b7ff1f159ea37e765d699b4871b403e079e9672c | c1ccccc1 | C-C-O-C(=O)-[CH;D3;+0:1](-[C:2](=[O;D1;H0:3])-[#8:4]-[C:5])-[C:6](=[O;D1;H0:7])-[c:8]:[c:9]:[c:10](-[O;H0;D2;+0:11]-C):[c:12](-[O;H0;D2;+0:13]-C):[c:14]>>[C:5]-[#8:4]-[C:2](=[O;D1;H0:3])-[CH2;D2;+0:1]-[C:6](=[O;D1;H0:7])-[c:8]:[c:9]:[c:10](-[OH;D1;+0:11]):[c:12](-[OH;D1;+0:13]):[c:14] | null | [] | null | null | 8 | HOUR | 20.1 g of diethyl (3,4-dimethoxy-5-nitrobenzoyl)-malonate are dissolved in 200 ml of methylene chloride, whereupon the solution is cooled to -20° and at this temperature there is added dropwise while stirring within 15 minutes a solution of 68.1 g of boron tribromide in 120 ml of methylene chloride. The mixture is subs... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester.Ester.Ether.Ether | Ketone.Ester.Aromatic alcohol.Aromatic alcohol | null | null | c1ccccc1 | HO- | C(Cl)Cl | null | 8 | CCOC(=O)C(C(=O)OCC)C(=O)c1cc(OC)c(OC)c([N+](=O)[O-])c1>C(Cl)Cl>CCOC(=O)CC(=O)c1cc(O)c(O)c([N+](=O)[O-])c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-6445255240324e9d8447953c0b0e269b | CCOC(=O)CC(=O)c1cc(O)c(O)c([N+](=O)[O-])c1.NN>>O=[N+]([O-])c1cc(-c2cc(O)[nH]n2)cc(O)c1O | OC=1C=C(C(=O)CC(=O)OCC)C=C(C1O)[N+](=O)[O-].O.NN>>OC1=CC(=NN1)C1=CC(=C(C(O)=C1)O)[N+](=O)[O-] | CCO[C:9]([CH2:8][C:7](=O)[c:6]1[cH:5][c:4]([N+:2](=[O:1])[O-:3])[c:16]([OH:17])[c:14]([OH:15])[cH:13]1)=[O:10].[NH2:11][NH2:12]>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6](-[c:7]2[cH:8][c:9]([OH:10])[nH:11][n:12]2)[cH:13][c:14]([OH:15])[c:16]1[OH:17] | CCOC(=O)CC(=O)c1cc(O)c(O)c([N+](=O)[O-])c1.NN | O=[N+]([O-])c1cc(-c2cc(O)[nH]n2)cc(O)c1O | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | fd057ffd397d0d2f3eb195e375be8e160bc07c7f239ab86634da2b8289d05677 | 0296f8f78a543918519351bd347834699f291cf4e6c7e504eef51f4e914155a4 | c1ccc(-c2cc[nH]n2)cc1 | C-C-O-[C;H0;D3;+0:1](=[O;H0;D1;+0:2])-[CH2;D2;+0:3]-[C;H0;D3;+0:4](=O)-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:8]:[c:9].[NH2;D1;+0:10]-[NH2;D1;+0:11]>>[OH;D1;+0:2]-[c;H0;D3;+0:1]1:[cH;D2;+0:3]:[c;H0;D3;+0:4](-[c;H0;D3;+0:5](:[c:6]:[c:7]):[c:8]:[c:9]):[n;H0;D2;+0:11]:[nH;D2;+0:10]:1 | null | [] | null | null | 5 | MINUTE | 2.0 g of ethyl (3,4-dihydroxy-5-nitrobenzoyl)acetate are suspended in 50 ml of ethanol. After treatment with 0.4 g of hydrazine hydrate the mixture is held at the reflux temperature for 16 hours. After distillation of the solvent, the residue is held at the boiling temperature for 5 minutes with 50 ml of ethyl acetate.... | 10.6084/m9.figshare.5104873.v1 | null | Hydrazine.Ketone.Ester | Aromatic alcohol | null | c1cn[nH]c1 | c1ccccc1.c1cn[nH]c1 | HO- | C(C)O | null | 0.083333 | CCOC(=O)CC(=O)c1cc(O)c(O)c([N+](=O)[O-])c1.NN>C(C)O>O=[N+]([O-])c1cc(-c2cc(O)[nH]n2)cc(O)c1O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ec38551a5786499e8975aaf437861770 | O=C(O)c1cc(O)c(O)c([N+](=O)[O-])c1>>CC(=O)Oc1cc(C(=O)O)cc([N+](=O)[O-])c1OC(C)=O | OC=1C=C(C(=O)O)C=C(C1O)[N+](=O)[O-]>>C(C)(=O)OC=1C=C(C(=O)O)C=C(C1OC(C)=O)[N+](=O)[O-] | [c:1]1([OH:4])[cH:6][c:7]([C:8](=[O:3])[OH:10])[cH:11][c:12]([N+:13](=[O:14])[O-:15])[c:16]1[OH:17]>>[CH3:1][C:2](=[O:3])[O:4][c:5]1[cH:6][c:7]([C:8](=[O:9])[OH:10])[cH:11][c:12]([N+:13](=[O:14])[O-:15])[c:16]1[O:17][C:18]([CH3:19])=[O:20] | O=C(O)c1cc(O)c(O)c([N+](=O)[O-])c1 | CC(=O)Oc1cc(C(=O)O)cc([N+](=O)[O-])c1OC(C)=O | null | null | C(C)(=O)OC(C)=O | Functional Group Addition | OtherReaction | dfc392141f92ea007b8f91f0a0eacf40eaf430fc6af8db4501248d32cb70774a | bb3dbf0feaa4ba3fe52962ea9481d9ff4f9b217ff3df58e75a4597c218af4972 | c1ccccc1 | [#7;+:1]-[c:2]1:[c:3]:[c:4](-[C;H0;D3;+0:5](-[O;D1;H1:6])=[O;H0;D1;+0:7]):[cH;D2;+0:8]:[c;H0;D3;+0:9](-[OH;D1;+0:10]):[c;H0;D3;+0:11]:1-[OH;D1;+0:12]>>[#7;+:1]-[c:2]1:[c:3]:[c:4](-[C;H0;D3;+0:5](=[O;D1;H0:13])-[O;D1;H1:6]):[cH;D2;+0:8]:[c:14](-[O;H0;D2;+0:10]-[C:15](-[CH3;D1;+0:9])=[O;H0;D1;+0:7]):[c;H0;D3;+0:11]:1-[O;... | null | [] | null | null | 8 | HOUR | 7.3 g of 3,4-dihydroxy-5-nitrobenzoic acid are treated with 30 ml of acetic anhydride, whereupon the mixture is held at the reflux temperature for 8 hours. The reaction mixture is poured on to ice. The separated precipitate is filtered under suction, washed with water and taken up in methylene chloride. The organic pha... | 10.6084/m9.figshare.5104873.v1 | null | Carboxylic acid.Aromatic alcohol.Aromatic alcohol | Carboxylic acid.Ester.Ester | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | C(C)(=O)OC(C)=O | null | 8 | O=C(O)c1cc(O)c(O)c([N+](=O)[O-])c1>C(C)(=O)OC(C)=O>CC(=O)Oc1cc(C(=O)O)cc([N+](=O)[O-])c1OC(C)=O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-92f28bfd8ce349898c350e2c071e0ffe | COc1cc([N+](=O)[O-])cc(C=O)c1OC>>O=Cc1cc([N+](=O)[O-])cc(O)c1O | COC1=C(C=O)C=C(C=C1OC)[N+](=O)[O-].Br>>OC1=C(C=O)C=C(C=C1O)[N+](=O)[O-] | C[O:11][c:10]1[cH:9][c:5]([N+:6](=[O:7])[O-:8])[cH:4][c:3]([CH:2]=[O:1])[c:12]1[O:13]C>>[O:1]=[CH:2][c:3]1[cH:4][c:5]([N+:6](=[O:7])[O-:8])[cH:9][c:10]([OH:11])[c:12]1[OH:13] | COc1cc([N+](=O)[O-])cc(C=O)c1OC | O=Cc1cc([N+](=O)[O-])cc(O)c1O | null | null | C(C)(=O)O | Deprotection | OtherReaction | a0f05885bbc65ae2846cad0ac34029941211b2ef3a426958b0c8aa83bb16fe86 | 9df751cd682ad9d54ed75d7313aaead6a019c5d37ede15c4672866d319b900ff | c1ccccc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4](-[O;H0;D2;+0:5]-C):[c:6]-[C:7]=[O;D1;H0:8]>>[O;D1;H0:8]=[C:7]-[c:6]:[c:4](-[OH;D1;+0:5]):[c:2](-[OH;D1;+0:1]):[c:3] | null | [] | null | null | 7 | HOUR | 10.0 g of 2,3-dimethoxy-5-nitrobenzaldehyde are treated with 50 ml of glacial acetic acid and 50 ml of constant-boiling hydrobromic acid and held at the reflux temperature for 7 hours. After treatment with ice the separated precipitate is filtered under suction, washed with water and taken up in ethyl acetate. The orga... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aromatic alcohol.Aromatic alcohol | null | null | c1ccccc1 | Other | C(C)(=O)O | null | 7 | COc1cc([N+](=O)[O-])cc(C=O)c1OC>C(C)(=O)O>O=Cc1cc([N+](=O)[O-])cc(O)c1O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-eee972f5dc494a2d80b1b2fbcd641890 | COc1cc(C#N)cc([N+](=O)[O-])c1OC.[N-]=[N+]=[N-]>>COc1cc(-c2nnn[nH]2)cc([N+](=O)[O-])c1O | [Cl-].[NH4+].[N-]=[N+]=[N-].[Na+].COC=1C=C(C#N)C=C(C1OC)[N+](=O)[O-].[Cl-].[NH4+].[N-]=[N+]=[N-].[Na+]>>COC1=C(C(=CC(=C1)C1=NN=NN1)[N+](=O)[O-])O | C[O:17][c:16]1[c:3]([O:2][CH3:1])[cH:4][c:5]([C:6]#[N:7])[cH:11][c:12]1[N+:13](=[O:14])[O-:15].[N-:8]=[N+:9]=[N-:10]>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][n:8][n:9][nH:10]2)[cH:11][c:12]([N+:13](=[O:14])[O-:15])[c:16]1[OH:17] | COc1cc(C#N)cc([N+](=O)[O-])c1OC.[N-]=[N+]=[N-] | COc1cc(-c2nnn[nH]2)cc([N+](=O)[O-])c1O | null | null | CN(C=O)C | Aromatic Heterocycle Formation | OtherReaction | c64598af02ca1f021de8b34f401bdac10c7b9e50f7927859abb4fb77da5cad24 | 250e6bc39236463a4769eb2fb5a63c6d3c6c241536b2ecadc986b43fd86a8162 | c1ccc(-c2nnn[nH]2)cc1 | C-[O;H0;D2;+0:1]-[c:2]1:[c:3]:[c:4]:[c;H0;D3;+0:5](-[C;H0;D2;+0:6]#[N;H0;D1;+0:7]):[c:8]:[c:9]:1.[N-;H0;D1:10]=[N+;H0;D2:11]=[N-;H0;D1:12]>>[OH;D1;+0:1]-[c:2]1:[c:3]:[c:4]:[c;H0;D3;+0:5](-[c;H0;D3;+0:6]2:[n;H0;D2;+0:7]:[n;H0;D2;+0:12]:[n;H0;D2;+0:11]:[nH;D2;+0:10]:2):[c:8]:[c:9]:1 | null | [] | null | null | 31 | HOUR | 4.0 g of 3,4-dimethoxy-5-nitro-benzonitrile are dissolved in 50 ml of dimethylformamide, whereupon the solution is treated with 1.66 g of ammonium chloride and 2.02 g of sodium azide and stirred at 125° for 31 hours. After in each case 8 and 15 hours the same amounts of ammonium chloride and sodium azide are added ther... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Nitrile | Aromatic alcohol | null | c1nnn[nH]1 | c1ccccc1.c1nnn[nH]1 | Other | CN(C=O)C | null | 31 | COc1cc(C#N)cc([N+](=O)[O-])c1OC.[N-]=[N+]=[N-]>CN(C=O)C>COc1cc(-c2nnn[nH]2)cc([N+](=O)[O-])c1O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-42795be49eb140038e959df5919e02bb | COc1cc(-c2nnn[nH]2)cc([N+](=O)[O-])c1O>>O=[N+]([O-])c1cc(-c2nnn[nH]2)cc(O)c1O | COC1=C(C(=CC(=C1)C1=NN=NN1)[N+](=O)[O-])O>>[N+](=O)([O-])C1=C(C(O)=CC(=C1)C1=NN=NN1)O | C[O:14][c:13]1[cH:12][c:6](-[c:7]2[n:8][n:9][n:10][nH:11]2)[cH:5][c:4]([N+:2](=[O:1])[O-:3])[c:15]1[OH:16]>>[O:1]=[N+:2]([O-:3])[c:4]1[cH:5][c:6](-[c:7]2[n:8][n:9][n:10][nH:11]2)[cH:12][c:13]([OH:14])[c:15]1[OH:16] | COc1cc(-c2nnn[nH]2)cc([N+](=O)[O-])c1O | O=[N+]([O-])c1cc(-c2nnn[nH]2)cc(O)c1O | null | null | Br | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | c1ccc(-c2nnn[nH]2)cc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 8 | HOUR | 4.0 g of 2-methoxy-6-nitro-4-(1H-tetrazol-5-yl)phenol are treated with 40 ml of constant-boiling hydrobromic acid, whereupon the mixture is stirred at 140° for 8 hours under a nitrogen atmosphere. After cooling, the mixture is poured on to ice. The separated precipitate is filtered under suction and recrystallized from... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.c1nnn[nH]1 | Other | Br | null | 8 | COc1cc(-c2nnn[nH]2)cc([N+](=O)[O-])c1O>Br>O=[N+]([O-])c1cc(-c2nnn[nH]2)cc(O)c1O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-7a73a09bdefb4653a5621a63ebf06519 | N#Cc1cc(O)c(O)c([N+](=O)[O-])c1.O=S(=O)(O)O>>NC(=O)c1cc(O)c(O)c([N+](=O)[O-])c1 | OC=1C=C(C#N)C=C(C1O)[N+](=O)[O-].S(O)(O)(=O)=O>>OC=1C=C(C(=O)N)C=C(C1O)[N+](=O)[O-] | [N:1]#[C:2][c:4]1[cH:5][c:6]([OH:7])[c:8]([OH:9])[c:10]([N+:11](=[O:12])[O-:13])[cH:14]1.O=S(=O)(O)[OH:3]>>[NH2:1][C:2](=[O:3])[c:4]1[cH:5][c:6]([OH:7])[c:8]([OH:9])[c:10]([N+:11](=[O:12])[O-:13])[cH:14]1 | N#Cc1cc(O)c(O)c([N+](=O)[O-])c1.O=S(=O)(O)O | NC(=O)c1cc(O)c(O)c([N+](=O)[O-])c1 | null | null | null | Heteroatom Alkylation and Arylation | OtherReaction | 1d1793919e847ed86dcb16487e62464531560dbf4782f9a5875bfe7e0477a3ec | d6f9d146e8ef95e62f1a3ab55a7e3b4ceec8856a5f71b6dccd4ad850f945b658 | c1ccccc1 | O-S(=O)(=O)-[OH;D1;+0:1].[N;H0;D1;+0:2]#[C;H0;D2;+0:3]-[c:4](:[c:5]):[c:6]>>[NH2;D1;+0:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:1])-[c:4](:[c:5]):[c:6] | null | [] | null | null | 10 | MINUTE | A total of 7.2 g of 3,4-dihydroxy-5-nitrobenzonitrile are introduced portionwise into 130 ml of conc. sulfuric acid while stirring within 10 minutes, whereupon the mixture is stirred at 50° for 4 hours. The reaction mixture is poured into 800 ml of ice-water. The separated precipitate is filtered under suction, washed ... | 10.6084/m9.figshare.5104873.v1 | null | Nitrile | Primary amide | null | null | c1ccccc1 | Other | null | null | 0.166667 | N#Cc1cc(O)c(O)c([N+](=O)[O-])c1.O=S(=O)(O)O>>NC(=O)c1cc(O)c(O)c([N+](=O)[O-])c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-1ea35317f98a4f45a0a861071d4c8123 | COc1cc(C(=O)Cl)cc([N+](=O)[O-])c1OC.O=C(CO)c1ccccc1>>COc1cc(C(=O)Oc2ccccc2C(C)=O)cc([N+](=O)[O-])c1OC | OCC(=O)C1=CC=CC=C1.[H-].[Na+].CN(C=O)C.CN(C=O)C.COC=1C=C(C(=O)Cl)C=C(C1OC)[N+](=O)[O-].CN(C=O)C>>COC=1C=C(C(=O)OC2=C(C=CC=C2)C(C)=O)C=C(C1OC)[N+](=O)[O-] | Cl[C:6]([c:5]1[cH:4][c:3]([O:2][CH3:1])[c:23]([O:24][CH3:25])[c:19]([N+:20](=[O:21])[O-:22])[cH:18]1)=[O:7].[OH:8][CH2:16][C:15]([c:14]1[cH:9][cH:10][cH:11][cH:12][cH:13]1)=[O:17]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[O:8][c:9]2[cH:10][cH:11][cH:12][cH:13][c:14]2[C:15]([CH3:16])=[O:17])[cH:18][c:19]([N+:20](=[O:... | COc1cc(C(=O)Cl)cc([N+](=O)[O-])c1OC.O=C(CO)c1ccccc1 | COc1cc(C(=O)Oc2ccccc2C(C)=O)cc([N+](=O)[O-])c1OC | null | null | C1(=CC=CC=C1)C | Acylation | OtherReaction | 6c40f4ced08eb853a926aef17ca3bf5b4b1494fcf48119bad0032a0c02d4e875 | 75868dd37a1cf5bb345efdd4a4faeb4c7ef032fe8663bba7c7b687cb7a2c764b | O=C(Oc1ccccc1)c1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[O;D1;H0:6]=[C:7](-[CH2;D2;+0:8]-[OH;D1;+0:9])-[c:10](:[c:11]):[cH;D2;+0:12]:[c:13]:[c:14]>>[CH3;D1;+0:8]-[C:7](=[O;D1;H0:6])-[c:10](:[c:11]):[c;H0;D3;+0:12](-[O;H0;D2;+0:9]-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5]):[c:13]:[c:14] | null | [] | null | null | 1 | HOUR | A solution of 11.25 g of 2-hydroxyacetophenone in 100 ml of absolute dimethylformamide is added dropwise under an argon atmosphere within 15 minutes to a suspension of 3.6 g of a 55 percent sodium hydride dispersion in 50 ml of absolute dimethylformamide and the mixture is stirred at room temperature for 1 hour. After ... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide.Ketone.Primary alcohol | Ketone.Ester | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HCl | C1(=CC=CC=C1)C | null | 1 | COc1cc(C(=O)Cl)cc([N+](=O)[O-])c1OC.O=C(CO)c1ccccc1>C1(=CC=CC=C1)C>COc1cc(C(=O)Oc2ccccc2C(C)=O)cc([N+](=O)[O-])c1OC |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-465ce0989cbe4d54964db86e3d958d51 | COc1cc(C(=O)CC(=O)c2ccccc2O)cc([N+](=O)[O-])c1OC>>O=C(CC(=O)c1ccccc1O)c1cc(O)c(O)c([N+](=O)[O-])c1 | B(Br)(Br)Br.OC1=C(C=CC=C1)C(CC(=O)C1=CC(=C(C(=C1)[N+](=O)[O-])OC)OC)=O.C(C)O>>OC=1C=C(C=C(C1O)[N+](=O)[O-])C(CC(=O)C1=C(C=CC=C1)O)=O | C[O:16][c:15]1[cH:14][c:13]([C:2](=[O:1])[CH2:3][C:4](=[O:5])[c:6]2[cH:7][cH:8][cH:9][cH:10][c:11]2[OH:12])[cH:23][c:19]([N+:20](=[O:21])[O-:22])[c:17]1[O:18]C>>[O:1]=[C:2]([CH2:3][C:4](=[O:5])[c:6]1[cH:7][cH:8][cH:9][cH:10][c:11]1[OH:12])[c:13]1[cH:14][c:15]([OH:16])[c:17]([OH:18])[c:19]([N+:20](=[O:21])[O-:22])[cH:23... | COc1cc(C(=O)CC(=O)c2ccccc2O)cc([N+](=O)[O-])c1OC | O=C(CC(=O)c1ccccc1O)c1cc(O)c(O)c([N+](=O)[O-])c1 | null | null | C(Cl)Cl | Deprotection | OtherReaction | a0f05885bbc65ae2846cad0ac34029941211b2ef3a426958b0c8aa83bb16fe86 | 9df751cd682ad9d54ed75d7313aaead6a019c5d37ede15c4672866d319b900ff | O=C(CC(=O)c1ccccc1)c1ccccc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4](-[O;H0;D2;+0:5]-C):[c:6]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4](-[OH;D1;+0:5]):[c:6] | null | [] | null | null | null | null | A solution of 1.82 g of boron tribromide in 20 ml of methylene chloride is added dropwise within about 20 minutes to a solution of 500 mg of 1-(o-hydroxyphenyl)-3-(3,4-dimethoxy-5-nitrophenyl)-1,3-propanedione in 50 ml of methylene chloride while stirring and under an argon atmosphere at -20°, whereupon the mixture is ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aromatic alcohol.Aromatic alcohol | null | null | c1ccccc1.c1ccccc1 | Other | C(Cl)Cl | null | null | COc1cc(C(=O)CC(=O)c2ccccc2O)cc([N+](=O)[O-])c1OC>C(Cl)Cl>O=C(CC(=O)c1ccccc1O)c1cc(O)c(O)c([N+](=O)[O-])c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-705ed834130c4adcb591f79eeb956aff | COc1cc(C(=O)Oc2ccccc2C(C)=O)cc([N+](=O)[O-])c1OC>>COc1cc(-c2cc(=O)c3ccccc3o2)cc([N+](=O)[O-])c1OC | COC=1C=C(C(=O)OC2=C(C=CC=C2)C(C)=O)C=C(C1OC)[N+](=O)[O-].C(C)(=O)[O-].[Na+]>>COC=1C=C(C=C(C1OC)[N+](=O)[O-])C=1OC2=C(C(C1)=O)C=CC=C2 | O=[C:6]([c:5]1[cH:4][c:3]([O:2][CH3:1])[c:22]([O:23][CH3:24])[c:18]([N+:19](=[O:20])[O-:21])[cH:17]1)[O:16][c:15]1[c:10]([C:8]([CH3:7])=[O:9])[cH:11][cH:12][cH:13][cH:14]1>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[cH:7][c:8](=[O:9])[c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[o:16]2)[cH:17][c:18]([N+:19](=[O:20])[O-:21])[c:... | COc1cc(C(=O)Oc2ccccc2C(C)=O)cc([N+](=O)[O-])c1OC | COc1cc(-c2cc(=O)c3ccccc3o2)cc([N+](=O)[O-])c1OC | null | null | C(C)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 5d20209306097825783ca9063e3d99a2c3db2f4c43630102fd047745af332133 | 90d91da8fe4a4df48cab6f211982834fddab85bdecacddc95412489737467fb5 | O=c1cc(-c2ccccc2)oc2ccccc12 | O=[C;H0;D3;+0:1](-[O;H0;D2;+0:2]-[c:3](:[c:4]):[c:5](-[C;H0;D3;+0:6](-[CH3;D1;+0:7])=[O;D1;H0:8]):[c:9])-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]>>[O;D1;H0:8]=[c;H0;D3;+0:6]1:[cH;D2;+0:7]:[c;H0;D3;+0:1](-[c;H0;D3;+0:10](:[c:11]:[c:12]):[c:13]:[c:14]):[o;H0;D2;+0:2]:[c:3](:[c:4]):[c:5]:1:[c:9] | null | [] | null | null | 4 | HOUR | A solution of 2.0 g of o-acetylphenyl 3,4-dimethoxy-5-nitrobenzoate in 12.5 ml of glacial acetic acid is treated with 0.94 g of sodium acetate and held at the reflux temperature for 4 hours. After cooling the mixture is poured into ice-water. The separated crystals are filtered under suction. After recrystallization fr... | 10.6084/m9.figshare.5104873.v1 | null | Ketone.Ester | null | c1ccccc1 | c1ccc2ccccc2o1 | c1ccccc1.c1ccc2ccccc2o1 | HO- | C(C)(=O)O | null | 4 | COc1cc(C(=O)Oc2ccccc2C(C)=O)cc([N+](=O)[O-])c1OC>C(C)(=O)O>COc1cc(-c2cc(=O)c3ccccc3o2)cc([N+](=O)[O-])c1OC |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-8fc69151ab994bba99b10abf15a5c2ed | COc1cc(-c2cc(=O)c3ccccc3o2)cc([N+](=O)[O-])c1OC>>O=c1cc(-c2cc(O)c(O)c([N+](=O)[O-])c2)oc2ccccc12 | B(Br)(Br)Br.COC=1C=C(C=C(C1OC)[N+](=O)[O-])C=1OC2=C(C(C1)=O)C=CC=C2.C(C)O>>OC=1C=C(C=C(C1O)[N+](=O)[O-])C=1OC2=C(C(C1)=O)C=CC=C2 | C[O:8][c:7]1[cH:6][c:5](-[c:4]2[cH:3][c:2](=[O:1])[c:22]3[c:17]([o:16]2)[cH:18][cH:19][cH:20][cH:21]3)[cH:15][c:11]([N+:12](=[O:13])[O-:14])[c:9]1[O:10]C>>[O:1]=[c:2]1[cH:3][c:4](-[c:5]2[cH:6][c:7]([OH:8])[c:9]([OH:10])[c:11]([N+:12](=[O:13])[O-:14])[cH:15]2)[o:16][c:17]2[cH:18][cH:19][cH:20][cH:21][c:22]12 | COc1cc(-c2cc(=O)c3ccccc3o2)cc([N+](=O)[O-])c1OC | O=c1cc(-c2cc(O)c(O)c([N+](=O)[O-])c2)oc2ccccc12 | null | null | C(Cl)Cl | Deprotection | OtherReaction | a0f05885bbc65ae2846cad0ac34029941211b2ef3a426958b0c8aa83bb16fe86 | 9df751cd682ad9d54ed75d7313aaead6a019c5d37ede15c4672866d319b900ff | O=c1cc(-c2ccccc2)oc2ccccc12 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4](-[O;H0;D2;+0:5]-C):[c:6]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4](-[OH;D1;+0:5]):[c:6] | null | [] | null | null | 8 | HOUR | A solution of 10 ml of boron tribromide in 50 ml of methylene chloride are added dropwise within 30 minutes at -10° to a solution of 1.0 g of 2-(3,4-dimethoxy-5-nitrophenyl)-4H-1-benzopyran-4-one in 100 ml of methylene chloride under an argon atmosphere, whereupon the mixture is stirred at room temperature overnight. A... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aromatic alcohol.Aromatic alcohol | null | null | c1ccccc1.c1ccc2ccccc2o1 | Other | C(Cl)Cl | null | 8 | COc1cc(-c2cc(=O)c3ccccc3o2)cc([N+](=O)[O-])c1OC>C(Cl)Cl>O=c1cc(-c2cc(O)c(O)c([N+](=O)[O-])c2)oc2ccccc12 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-89e48e9199d148b6b87276776a95bd83 | COc1cc(C=O)ccc1OCc1ccccc1.FC(F)(F)c1ccc(Br)cc1>>COc1cc(C(O)c2ccc(C(F)(F)F)cc2)ccc1OCc1ccccc1 | C(CCC)[Li].BrC1=CC=C(C=C1)C(F)(F)F.COC=1C=C(C=O)C=CC1OCC1=CC=CC=C1>>C(C1=CC=CC=C1)OC1=C(C=C(C(C2=CC=C(C=C2)C(F)(F)F)O)C=C1)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]=[O:7])[cH:18][cH:19][c:20]1[O:21][CH2:22][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1.Br[c:8]1[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][cH:17]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]([OH:7])[c:8]2[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][cH:17]2)[cH:18][c... | COc1cc(C=O)ccc1OCc1ccccc1.FC(F)(F)c1ccc(Br)cc1 | COc1cc(C(O)c2ccc(C(F)(F)F)cc2)ccc1OCc1ccccc1 | null | null | S(O)(O)(=O)=O | C-C Coupling | Grignard_alcohol | 0c8bc0f755f4d9a2cfce93ae43a9a9a531fa8ad86ff120aed0a18ba03c84e4d7 | 1c0bd0afc1d5e370e3c8193faf738f03752295e40fa0eb99c756011e9a4be26b | c1ccc(COc2ccc(Cc3ccccc3)cc2)cc1 | Br-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5].[O;H0;D1;+0:6]=[CH;D2;+0:7]-[c:8](:[c:9]):[c:10]>>[OH;D1;+0:6]-[CH;D3;+0:7](-[c:8](:[c:9]):[c:10])-[c;H0;D3;+0:1](:[c:2]:[c:3]):[c:4]:[c:5] | null | [] | null | null | 45 | MINUTE | 92 ml of n-butyl lithium solution (1.6M in hexane) are added dropwise at -70° within 20 minutes to 33.0 g of 4-bromobenzotrifluoride (dissolved in 150 ml of tetrahydrofuran). After stirring at -70° for 45 minutes, 36 g of 3-methoxy-4-benzyloxybenzaldehyde (dissolved in 100 ml of tetrahydrofuran) are added dropwise ther... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aldehyde | Secondary alcohol | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1.c1ccccc1 | Br- | S(O)(O)(=O)=O | null | 0.75 | COc1cc(C=O)ccc1OCc1ccccc1.FC(F)(F)c1ccc(Br)cc1>S(O)(O)(=O)=O>COc1cc(C(O)c2ccc(C(F)(F)F)cc2)ccc1OCc1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-c48e541fe4664b73b041f82e2e092d87 | COc1cc(C(O)c2ccc(C(F)(F)F)cc2)ccc1OCc1ccccc1>>COc1cc(C(=O)c2ccc(C(F)(F)F)cc2)ccc1OCc1ccccc1 | [Cr](=O)(=O)([O-])Cl.[NH+]1=CC=CC=C1.C(C1=CC=CC=C1)OC1=C(C=C(C(C2=CC=C(C=C2)C(F)(F)F)O)C=C1)OC>>C(C1=CC=CC=C1)OC1=C(C=C(C(=O)C2=CC=C(C=C2)C(F)(F)F)C=C1)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]([OH:7])[c:8]2[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][cH:17]2)[cH:18][cH:19][c:20]1[O:21][CH2:22][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[c:8]2[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][cH:17]2)[cH:18][cH:... | COc1cc(C(O)c2ccc(C(F)(F)F)cc2)ccc1OCc1ccccc1 | COc1cc(C(=O)c2ccc(C(F)(F)F)cc2)ccc1OCc1ccccc1 | null | null | null | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | c7c20d2959ac48847b03cc1265962cf99a8ec8a85900c087dabb30077298c66c | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | O=C(c1ccccc1)c1ccc(OCc2ccccc2)cc1 | [OH;D1;+0:1]-[CH;D3;+0:2](-[c:3](:[c:4]):[c:5])-[c:6](:[c:7]):[c:8]>>[O;H0;D1;+0:1]=[C;H0;D3;+0:2](-[c:3](:[c:4]):[c:5])-[c:6](:[c:7]):[c:8] | null | [] | null | null | 2 | HOUR | 52.6 g of 4-(benzyloxy)-3-methoxy-4'-(trifluoromethyl)benzhydrol (dissolved in 500 ml of methylene chloride) are treated within 10 minutes at 20° with 30.6 g of pyridinium chlorochromate and stirred at 20° for 2 hours. The precipitate formed is subsequently filtered and washed with methylene chloride. The filtrate is e... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | null | null | null | 2 | COc1cc(C(O)c2ccc(C(F)(F)F)cc2)ccc1OCc1ccccc1>>COc1cc(C(=O)c2ccc(C(F)(F)F)cc2)ccc1OCc1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-04a8adaeb4b34aca93fd522bb77b7762 | COc1cc(C(=O)c2ccc(C(F)(F)F)cc2)ccc1OCc1ccccc1>>COc1cc(C(=O)c2ccc(C(F)(F)F)cc2)ccc1O | Br.C(C1=CC=CC=C1)OC1=C(C=C(C(=O)C2=CC=C(C=C2)C(F)(F)F)C=C1)OC>>OC1=C(C=C(C(=O)C2=CC=C(C=C2)C(F)(F)F)C=C1)OC | c1ccc(C[O:21][c:20]2[c:3]([O:2][CH3:1])[cH:4][c:5]([C:6](=[O:7])[c:8]3[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][cH:17]3)[cH:18][cH:19]2)cc1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[c:8]2[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][cH:17]2)[cH:18][cH:19][c:20]1[OH:21] | COc1cc(C(=O)c2ccc(C(F)(F)F)cc2)ccc1OCc1ccccc1 | COc1cc(C(=O)c2ccc(C(F)(F)F)cc2)ccc1O | null | null | C(C)(=O)O | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C(c1ccccc1)c1ccccc1 | [c:1]:[c:2](-[O;H0;D2;+0:3]-C-c1:c:c:c:c:c:1):[c:4]>>[OH;D1;+0:3]-[c:2](:[c:1]):[c:4] | null | [] | null | null | 1.5 | HOUR | 70 ml. of 33 percent hydrobromic acid in acetic acid are added within 15 minutes at 10° to 20 g of 4-(benzyloxy)-3-methoxy-4'-(trifluoromethyl)benzophenone (dissolved in 150 ml of methylene chloride). After stirring at 20° for 1.5 hours, the reaction mixture is poured into 600 ml. of ice-water; the methylene chloride p... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1ccccc1.c1ccccc1 | Other | C(C)(=O)O | null | 1.5 | COc1cc(C(=O)c2ccc(C(F)(F)F)cc2)ccc1OCc1ccccc1>C(C)(=O)O>COc1cc(C(=O)c2ccc(C(F)(F)F)cc2)ccc1O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-0898ca40f5d84799a1ce9a4471a5d83b | COc1cc(C(=O)c2ccc(C(F)(F)F)cc2)ccc1O.O=[N+]([O-])O>>COc1cc(C(=O)c2ccc(C(F)(F)F)cc2)cc([N+](=O)[O-])c1O | [N+](=O)(O)[O-].OC1=C(C=C(C(=O)C2=CC=C(C=C2)C(F)(F)F)C=C1)OC>>OC1=C(C=C(C(=O)C2=CC=C(C=C2)C(F)(F)F)C=C1[N+](=O)[O-])OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[c:8]2[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][cH:17]2)[cH:18][cH:19][c:23]1[OH:24].O[N+:20](=[O:21])[O-:22]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[c:8]2[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][cH:17]2)[cH:18][c:19]([N+:20](=[O:21])[O-:22]... | COc1cc(C(=O)c2ccc(C(F)(F)F)cc2)ccc1O.O=[N+]([O-])O | COc1cc(C(=O)c2ccc(C(F)(F)F)cc2)cc([N+](=O)[O-])c1O | null | null | null | Functional Group Addition | Aromatic nitration with HNO3 | 53848b8b2bb4e867226e49db2e60519b24be9379900e3ad7c56af54fe8fde7a5 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | O=C(c1ccccc1)c1ccccc1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[O;D1;H0:4]=[C:5]-[c:6]:[c:7]:[cH;D2;+0:8]:[c:9](-[O;D1;H1:10]):[c:11]>>[O;-;D1;H0:2]-[N+;H0;D3:1](=[O;D1;H0:3])-[c;H0;D3;+0:8](:[c:7]:[c:6]-[C:5]=[O;D1;H0:4]):[c:9](-[O;D1;H1:10]):[c:11] | null | [] | null | null | 1.5 | HOUR | 3.2 ml of 65 percent nitric acid are added dropwise within 10 minutes at 20° to 12.8 g of 4-hydroxy-3-methoxy-4'-(trifluoromethyl)benzophenone (dissolved in 160 ml of acetic acid). After stirring for 1.5 hours, the reaction mixture is poured into 600 ml of ice-water, and the precipitate formed is filtered off, washed w... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HO- | null | null | 1.5 | COc1cc(C(=O)c2ccc(C(F)(F)F)cc2)ccc1O.O=[N+]([O-])O>>COc1cc(C(=O)c2ccc(C(F)(F)F)cc2)cc([N+](=O)[O-])c1O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-582de6184de2448c8d4a8c9d6018b2f0 | COc1cc(C(=O)c2ccc(C(F)(F)F)cc2)cc([N+](=O)[O-])c1O>>O=C(c1ccc(C(F)(F)F)cc1)c1cc(O)c(O)c([N+](=O)[O-])c1 | OC1=C(C=C(C(=O)C2=CC=C(C=C2)C(F)(F)F)C=C1[N+](=O)[O-])OC>>OC=1C=C(C(=O)C2=CC=C(C=C2)C(F)(F)F)C=C(C1O)[N+](=O)[O-] | C[O:16][c:15]1[cH:14][c:13]([C:2](=[O:1])[c:3]2[cH:4][cH:5][c:6]([C:7]([F:8])([F:9])[F:10])[cH:11][cH:12]2)[cH:23][c:19]([N+:20](=[O:21])[O-:22])[c:17]1[OH:18]>>[O:1]=[C:2]([c:3]1[cH:4][cH:5][c:6]([C:7]([F:8])([F:9])[F:10])[cH:11][cH:12]1)[c:13]1[cH:14][c:15]([OH:16])[c:17]([OH:18])[c:19]([N+:20](=[O:21])[O-:22])[cH:23... | COc1cc(C(=O)c2ccc(C(F)(F)F)cc2)cc([N+](=O)[O-])c1O | O=C(c1ccc(C(F)(F)F)cc1)c1cc(O)c(O)c([N+](=O)[O-])c1 | null | null | Br | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C(c1ccccc1)c1ccccc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 18 | HOUR | 2.0 g of 4-hydroxy-3-methoxy-5-nitro-4'-(trifluoromethyl)benzophenone (dissolved in 20 ml of 33 percent hydrobromic acid in glacial acetic acid) are stirred at 90° for 18 hours. Thereupon. 20 ml of 48 percent aqueous hydrobromic acid are added thereto, whereupon the mixture is stirred at 110° for an additional 18 hours... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.c1ccccc1 | Other | Br | null | 18 | COc1cc(C(=O)c2ccc(C(F)(F)F)cc2)cc([N+](=O)[O-])c1O>Br>O=C(c1ccc(C(F)(F)F)cc1)c1cc(O)c(O)c([N+](=O)[O-])c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-f71597bc298048259985d406149e3738 | COc1cc(C(=O)c2ccc(C(F)(F)F)cc2)cc([N+](=O)[O-])c1OC>>COc1cc(C(=O)c2ccc(C(F)(F)F)cc2)cc(N)c1OC | O.O.[Sn](Cl)Cl.COC=1C=C(C(=O)C2=CC=C(C=C2)C(F)(F)F)C=C(C1OC)[N+](=O)[O-].[OH-].[Na+]>>NC=1C(=C(C=C(C(=O)C2=CC=C(C=C2)C(F)(F)F)C1)OC)OC | O=[N+:20]([O-])[c:19]1[cH:18][c:5]([C:6](=[O:7])[c:8]2[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][cH:17]2)[cH:4][c:3]([O:2][CH3:1])[c:21]1[O:22][CH3:23]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[c:8]2[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][cH:17]2)[cH:18][c:19]([NH2:20])[c:21]1[O:22][CH... | COc1cc(C(=O)c2ccc(C(F)(F)F)cc2)cc([N+](=O)[O-])c1OC | COc1cc(C(=O)c2ccc(C(F)(F)F)cc2)cc(N)c1OC | null | null | null | Reduction | Reduction of nitro groups to amines | bbc242b150a51e69d3ad1caaa391f4422710431b398dcb880555f476706790be | 7b0317532ea57a4fcedc1efc3e3c22eb5238d1c8330da53d4f9801fc2391f567 | O=C(c1ccccc1)c1ccccc1 | O=[N+;H0;D3:1](-[O-])-[c:2](:[c:3]):[c:4]>>[NH2;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 30 | MINUTE | 49.5 g of tin dichloride dihydrate are added to 16.0 g of 3,4-dimethoxy-5-nitro-4'-(trifluoromethyl)benzophenone (dissolved in 300 ml of ethanol). whereupon the mixture is stirred at 75° for 30 minutes. Thereupon, the reaction mixture is poured into 800 ml of ice-water. It is neutralized with 28 percent sodium hydroxid... | 10.6084/m9.figshare.5104873.v1 | null | Nitro group | Primary amine | null | null | c1ccccc1.c1ccccc1 | Other | null | null | 0.5 | COc1cc(C(=O)c2ccc(C(F)(F)F)cc2)cc([N+](=O)[O-])c1OC>>COc1cc(C(=O)c2ccc(C(F)(F)F)cc2)cc(N)c1OC |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-58dcac447e6842439c8d26a0a1eef59d | COc1cc(C(=O)c2ccc(C(F)(F)F)cc2)cc(C#N)c1OC>>N#Cc1cc(C(=O)c2ccc(C(F)(F)F)cc2)cc(O)c1O | C(#N)C=1C(=C(C=C(C(=O)C2=CC=C(C=C2)C(F)(F)F)C1)OC)OC.B(Br)(Br)Br.CO>>C(#N)C=1C(=C(C=C(C(=O)C2=CC=C(C=C2)C(F)(F)F)C1)O)O | C[O:20][c:19]1[cH:18][c:5]([C:6](=[O:7])[c:8]2[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][cH:17]2)[cH:4][c:3]([C:2]#[N:1])[c:21]1[O:22]C>>[N:1]#[C:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[c:8]2[cH:9][cH:10][c:11]([C:12]([F:13])([F:14])[F:15])[cH:16][cH:17]2)[cH:18][c:19]([OH:20])[c:21]1[OH:22] | COc1cc(C(=O)c2ccc(C(F)(F)F)cc2)cc(C#N)c1OC | N#Cc1cc(C(=O)c2ccc(C(F)(F)F)cc2)cc(O)c1O | null | null | C(Cl)Cl | Deprotection | OtherReaction | a0f05885bbc65ae2846cad0ac34029941211b2ef3a426958b0c8aa83bb16fe86 | 9df751cd682ad9d54ed75d7313aaead6a019c5d37ede15c4672866d319b900ff | O=C(c1ccccc1)c1ccccc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4](-[O;H0;D2;+0:5]-C):[c:6]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4](-[OH;D1;+0:5]):[c:6] | null | [] | null | null | 18 | HOUR | 1.5 g of 5-cyano-3,4-dimethoxy-4'-(trifluoromethyl)benzophenone (dissolved in 75 ml of methylene chloride) are treated at 5° with 2.18 ml of boron tribromide, whereupon the mixture is stirred at room temperature for 18 hours. The reaction mixture is subsequently diluted with 50 ml of methylene chloride. The mixture is ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aromatic alcohol.Aromatic alcohol | null | null | c1ccccc1.c1ccccc1 | Other | C(Cl)Cl | null | 18 | COc1cc(C(=O)c2ccc(C(F)(F)F)cc2)cc(C#N)c1OC>C(Cl)Cl>N#Cc1cc(C(=O)c2ccc(C(F)(F)F)cc2)cc(O)c1O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-e9a6adc5fe0f41249ef5dc7a9e206915 | COc1cc(C(=O)Cl)cc([N+](=O)[O-])c1OC.Cn1ccnc1>>COc1cc(C(=O)c2nccn2C)cc([N+](=O)[O-])c1OC | [OH-].[Na+].COC=1C=C(C(=O)Cl)C=C(C1OC)[N+](=O)[O-].CN1C=NC=C1.C(C)N(CC)CC>>CN1C(=NC=C1)C(=O)C1=CC(=C(C(=C1)[N+](=O)[O-])OC)OC | Cl[C:6]([c:5]1[cH:4][c:3]([O:2][CH3:1])[c:19]([O:20][CH3:21])[c:15]([N+:16](=[O:17])[O-:18])[cH:14]1)=[O:7].[cH:8]1[n:9][cH:10][cH:11][n:12]1[CH3:13]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[c:8]2[n:9][cH:10][cH:11][n:12]2[CH3:13])[cH:14][c:15]([N+:16](=[O:17])[O-:18])[c:19]1[O:20][CH3:21] | COc1cc(C(=O)Cl)cc([N+](=O)[O-])c1OC.Cn1ccnc1 | COc1cc(C(=O)c2nccn2C)cc([N+](=O)[O-])c1OC | null | null | N1=CC=CC=C1 | C-C Coupling | Friedel-Crafts acylation | db21c1d8b31fada511e06d819b13aabb5ba6195cf8ea6b5d0b43ee9de27776e1 | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | O=C(c1ccccc1)c1ncc[nH]1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C;D1;H3:6]-[#7;a:7]1:[c:8]:[c:9]:[#7;a:10]:[cH;D2;+0:11]:1>>[C;D1;H3:6]-[#7;a:7]1:[c:8]:[c:9]:[#7;a:10]:[c;H0;D3;+0:11]:1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 3 | HOUR | A solution of 16.0 g of 3,4-dimethoxy-5-nitrobenzoyl chloride in 80 ml of pyridine is added dropwise to a solution of 2.68 g of 1-methylimidazole and 6.6 g of triethylamine in 80 ml of pyridine, whereupon the mixture is stirred at 60° for 3 hours. After treatment with 1.70 ml of 3N sodium hydroxide solution the mixture... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | c1c[nH]cn1 | c1ncc[nH]1 | c1ccccc1.c1ncc[nH]1 | HCl | N1=CC=CC=C1 | null | 3 | COc1cc(C(=O)Cl)cc([N+](=O)[O-])c1OC.Cn1ccnc1>N1=CC=CC=C1>COc1cc(C(=O)c2nccn2C)cc([N+](=O)[O-])c1OC |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-0ad41fd7dd0c4f0bab6d9b0645b978f4 | COc1cc(C(=O)c2nccn2C)cc([N+](=O)[O-])c1OC>>Cn1ccnc1C(=O)c1cc(O)c(O)c([N+](=O)[O-])c1 | CN1C(=NC=C1)C(=O)C1=CC(=C(C(=C1)[N+](=O)[O-])OC)OC.Br>>Br.CN1C(=NC=C1)C(=O)C1=CC(=C(C(=C1)[N+](=O)[O-])O)O | C[O:13][c:12]1[cH:11][c:10]([C:8]([c:7]2[n:3]([CH3:2])[cH:4][cH:5][n:6]2)=[O:9])[cH:20][c:16]([N+:17](=[O:18])[O-:19])[c:14]1[O:15]C>>[CH3:2][n:3]1[cH:4][cH:5][n:6][c:7]1[C:8](=[O:9])[c:10]1[cH:11][c:12]([OH:13])[c:14]([OH:15])[c:16]([N+:17](=[O:18])[O-:19])[cH:20]1 | COc1cc(C(=O)c2nccn2C)cc([N+](=O)[O-])c1OC | Cn1ccnc1C(=O)c1cc(O)c(O)c([N+](=O)[O-])c1 | null | null | null | Deprotection | OtherReaction | a0f05885bbc65ae2846cad0ac34029941211b2ef3a426958b0c8aa83bb16fe86 | 9df751cd682ad9d54ed75d7313aaead6a019c5d37ede15c4672866d319b900ff | O=C(c1ccccc1)c1ncc[nH]1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4](-[O;H0;D2;+0:5]-C):[c:6]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4](-[OH;D1;+0:5]):[c:6] | null | [] | null | null | null | null | 5.0 g of 3,4-dimethoxy-5-nitrophenyl (1-methylimidazol-2-yl) ketone are treated with 50 ml of hydrobromic acid (48%), whereupon the mixture is stirred under reflux temperature for 2 hours. After cooling the separated precipitate is filtered under suction, washed with ice-water and recrystallized from ethanol. There is ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aromatic alcohol.Aromatic alcohol | null | null | c1ncc[nH]1.c1ccccc1 | Other | null | null | null | COc1cc(C(=O)c2nccn2C)cc([N+](=O)[O-])c1OC>>Cn1ccnc1C(=O)c1cc(O)c(O)c([N+](=O)[O-])c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-48181e52aad74c4986444be96aca97cc | COc1cc(C(=O)Cl)cc([N+](=O)[O-])c1OC.c1ccc(COCn2ccnc2)cc1>>COc1cc(C(=O)c2nccn2COCc2ccccc2)cc([N+](=O)[O-])c1OC | COC=1C=C(C(=O)Cl)C=C(C1OC)[N+](=O)[O-].C(C)N(CC)CC.C(C1=CC=CC=C1)OCN1C=NC=C1>>COC=1C=C(C=C(C1OC)[N+](=O)[O-])C(=O)C=1N(C=CN1)COCC1=CC=CC=C1 | Cl[C:6]([c:5]1[cH:4][c:3]([O:2][CH3:1])[c:27]([O:28][CH3:29])[c:23]([N+:24](=[O:25])[O-:26])[cH:22]1)=[O:7].[cH:8]1[n:9][cH:10][cH:11][n:12]1[CH2:13][O:14][CH2:15][c:16]1[cH:17][cH:18][cH:19][cH:20][cH:21]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[c:8]2[n:9][cH:10][cH:11][n:12]2[CH2:13][O:14][CH2:15][c:16]2[cH:17][... | COc1cc(C(=O)Cl)cc([N+](=O)[O-])c1OC.c1ccc(COCn2ccnc2)cc1 | COc1cc(C(=O)c2nccn2COCc2ccccc2)cc([N+](=O)[O-])c1OC | null | null | C(C)#N | C-C Coupling | Friedel-Crafts acylation | db21c1d8b31fada511e06d819b13aabb5ba6195cf8ea6b5d0b43ee9de27776e1 | fe2a4a0dfbb5b71b9a065e092364c64b22b4eb1ad4d6ba2a1e8edc9d31fce3e4 | O=C(c1ccccc1)c1nccn1COCc1ccccc1 | Cl-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5].[C:6]-[#7;a:7]1:[c:8]:[c:9]:[#7;a:10]:[cH;D2;+0:11]:1>>[C:6]-[#7;a:7]1:[c:8]:[c:9]:[#7;a:10]:[c;H0;D3;+0:11]:1-[C;H0;D3;+0:1](=[O;D1;H0:2])-[c:3](:[c:4]):[c:5] | null | [] | null | null | 3 | HOUR | A solution of 10.0 g of 1-[(benzyloxy)- methyl]imidazole in 50 ml of acetonitrile is added dropwise within 10 minutes while cooling with ice to a solution of 13.0 g of 3,4-dimethoxy-5-nitrobenzoyl chloride and 5.4 g of triethylamine in 80 ml of acetonitrile so that the temperature does not exceed 25°. The mixture is su... | 10.6084/m9.figshare.5104873.v1 | null | Acyl halide | Ketone | c1c[nH]cn1 | c1ncc[nH]1 | c1ccccc1.c1ncc[nH]1.c1ccccc1 | HCl | C(C)#N | null | 3 | COc1cc(C(=O)Cl)cc([N+](=O)[O-])c1OC.c1ccc(COCn2ccnc2)cc1>C(C)#N>COc1cc(C(=O)c2nccn2COCc2ccccc2)cc([N+](=O)[O-])c1OC |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ae1df2f0afa3492d908f463ee5bf9dfb | Brc1cnc2ccccc2c1.COc1cc(C=O)ccc1OCc1ccccc1>>COc1cc(C(O)c2cnc3ccccc3c2)ccc1OCc1ccccc1 | C(CCC)[Li].BrC=1C=NC2=CC=CC=C2C1.C(C1=CC=CC=C1)OC1=C(C=C(C=O)C=C1)OC>>C(C1=CC=CC=C1)OC1=C(C=C(C=C1)C(O)C=1C=NC2=CC=CC=C2C1)OC | Br[c:8]1[cH:9][n:10][c:11]2[cH:12][cH:13][cH:14][cH:15][c:16]2[cH:17]1.[CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]=[O:7])[cH:18][cH:19][c:20]1[O:21][CH2:22][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]([OH:7])[c:8]2[cH:9][n:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[cH:17]2)[cH:18][cH:19... | Brc1cnc2ccccc2c1.COc1cc(C=O)ccc1OCc1ccccc1 | COc1cc(C(O)c2cnc3ccccc3c2)ccc1OCc1ccccc1 | null | null | CCOCC | C-C Coupling | Grignard_alcohol | bb9228c17090dcd2e4bea7dde2843576d0e528414eb941d859060f7061330fb5 | 1c0bd0afc1d5e370e3c8193faf738f03752295e40fa0eb99c756011e9a4be26b | c1ccc(COc2ccc(Cc3cnc4ccccc4c3)cc2)cc1 | Br-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1.[O;H0;D1;+0:7]=[CH;D2;+0:8]-[c:9](:[c:10]):[c:11]>>[OH;D1;+0:7]-[CH;D3;+0:8](-[c:9](:[c:10]):[c:11])-[c;H0;D3;+0:1]1:[c:2]:[c:3]:[c:4]:[#7;a:5]:[c:6]:1 | null | [] | null | null | 10 | MINUTE | A solution of 25.0 g of 3-bromoquinoline is dissolved in 200 ml of dry ether and cooled to -60°. At this temperature there are added dropwise within 15 minutes 75.1 ml of a 1.6 molar solution of n-butyllithium, whereupon the mixture is stirred for 10 minutes. A solution of 26.5 g of vanillin benzyl ether in 250 ml of d... | 10.6084/m9.figshare.5104873.v1 | null | Aromatic halide.Aldehyde | Secondary alcohol | c1ccc2ncccc2c1 | c1ccc2ncccc2c1 | c1ccccc1.c1ccc2ncccc2c1.c1ccccc1 | Br- | CCOCC | null | 0.166667 | Brc1cnc2ccccc2c1.COc1cc(C=O)ccc1OCc1ccccc1>CCOCC>COc1cc(C(O)c2cnc3ccccc3c2)ccc1OCc1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-998bf90d6aae423683039cf86728967d | COc1cc(C(O)c2cnc3ccccc3c2)ccc1OCc1ccccc1>>COc1cc(C(=O)c2cnc3ccccc3c2)ccc1OCc1ccccc1 | C(C1=CC=CC=C1)OC1=C(C=C(C=C1)C(O)C=1C=NC2=CC=CC=C2C1)OC.CCCCC>>N1=CC(=CC2=CC=CC=C12)C(=O)C1=CC(=C(C=C1)OCC1=CC=CC=C1)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]([OH:7])[c:8]2[cH:9][n:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[cH:17]2)[cH:18][cH:19][c:20]1[O:21][CH2:22][c:23]1[cH:24][cH:25][cH:26][cH:27][cH:28]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[c:8]2[cH:9][n:10][c:11]3[cH:12][cH:13][cH:14][cH:15][c:16]3[cH:17]2)[cH:18][cH:19][... | COc1cc(C(O)c2cnc3ccccc3c2)ccc1OCc1ccccc1 | COc1cc(C(=O)c2cnc3ccccc3c2)ccc1OCc1ccccc1 | null | [O-2].[O-2].[Mn+4] | CCOCC.C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | c7c20d2959ac48847b03cc1265962cf99a8ec8a85900c087dabb30077298c66c | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | O=C(c1ccc(OCc2ccccc2)cc1)c1cnc2ccccc2c1 | [OH;D1;+0:1]-[CH;D3;+0:2](-[c:3](:[c:4]):[c:5])-[c:6](:[c:7]):[c:8]:[#7;a:9]:[c:10]>>[O;H0;D1;+0:1]=[C;H0;D3;+0:2](-[c:3](:[c:4]):[c:5])-[c:6](:[c:7]):[c:8]:[#7;a:9]:[c:10] | null | [] | null | null | 2 | HOUR | A solution of 6.2 g of α-[4-(benzyloxy)-3-methoxyphenyl]-3-quinolinemethanol in 200 ml of methylene chloride is treated with 62 g of manganese dioxide and stirred at the reflux temperature 2 hours. After cooling the precipitate is filtered under suction and washed with methylene chloride. The filtrate is evaporated and... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | null | null | c1ccccc1.c1ccc2ncccc2c1.c1ccccc1 | null | [O-2].[O-2].[Mn+4].CCOCC.C(Cl)Cl | null | 2 | COc1cc(C(O)c2cnc3ccccc3c2)ccc1OCc1ccccc1>[O-2].[O-2].[Mn+4].CCOCC.C(Cl)Cl>COc1cc(C(=O)c2cnc3ccccc3c2)ccc1OCc1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-4fc45fe431c548d7b426c04fca9717f0 | COc1cc(C(=O)c2cnc3ccccc3c2)cc([N+](=O)[O-])c1O>>O=C(c1cc(O)c(O)c([N+](=O)[O-])c1)c1cnc2ccccc2c1 | N1=CC(=CC2=CC=CC=C12)C(=O)C1=CC(=C(C(=C1)[N+](=O)[O-])O)OC.Br>>Br.N1=CC(=CC2=CC=CC=C12)C(=O)C1=CC(=C(C(=C1)[N+](=O)[O-])O)O | C[O:7][c:6]1[cH:5][c:4]([C:3](=[O:2])[c:15]2[cH:16][n:17][c:18]3[cH:19][cH:20][cH:21][cH:22][c:23]3[cH:24]2)[cH:14][c:10]([N+:11](=[O:12])[O-:13])[c:8]1[OH:9]>>[O:2]=[C:3]([c:4]1[cH:5][c:6]([OH:7])[c:8]([OH:9])[c:10]([N+:11](=[O:12])[O-:13])[cH:14]1)[c:15]1[cH:16][n:17][c:18]2[cH:19][cH:20][cH:21][cH:22][c:23]2[cH:24]1 | COc1cc(C(=O)c2cnc3ccccc3c2)cc([N+](=O)[O-])c1O | O=C(c1cc(O)c(O)c([N+](=O)[O-])c1)c1cnc2ccccc2c1 | null | null | null | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C(c1ccccc1)c1cnc2ccccc2c1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | 3 | HOUR | 820 mg of 4-hydroxy-3-methoxy-5-nitrophenyl (3-quinolinyl) ketone are treated with 50 ml of 48 percent hydrobromic acid and held at the reflux temperature for 3 hours. After distillation of the hydrobromic acid at 50°, the residue is treated with 70 ml of hot water and the insoluble constituent is filtered under suctio... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.c1ccc2ncccc2c1 | Other | null | null | 3 | COc1cc(C(=O)c2cnc3ccccc3c2)cc([N+](=O)[O-])c1O>>O=C(c1cc(O)c(O)c([N+](=O)[O-])c1)c1cnc2ccccc2c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-aaf8321145ef4b5b877dc544623b30c4 | BrCCCc1ccccc1.COc1cc(C=O)ccc1OCc1ccccc1>>COc1cc(C(O)CCCc2ccccc2)ccc1OCc1ccccc1 | C(C1=CC=CC=C1)OC1=C(C=C(C=O)C=C1)OC.C1(=CC=CC=C1)CCCBr.C(C)(C)(C)[Li]>>C(C1=CC=CC=C1)OC1=C(C=C(C(CCCC2=CC=CC=C2)O)C=C1)OC | Br[CH2:8][CH2:9][CH2:10][c:11]1[cH:12][cH:13][cH:14][cH:15][cH:16]1.[CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]=[O:7])[cH:17][cH:18][c:19]1[O:20][CH2:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]([OH:7])[CH2:8][CH2:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17][cH:18][c:19... | BrCCCc1ccccc1.COc1cc(C=O)ccc1OCc1ccccc1 | COc1cc(C(O)CCCc2ccccc2)ccc1OCc1ccccc1 | null | null | CCOCC.CCCCC | C-C Coupling | Grignard_alcohol | 983d8b8e9b89ba290d93feeffe843caf411eba49bd1aefb21a784058d86f3a30 | 3e80fe0b4a87df3724831714de4ab23fef101254d00d9b3074e300e6e8f4b9ea | c1ccc(CCCCc2ccc(OCc3ccccc3)cc2)cc1 | Br-[CH2;D2;+0:1]-[C:2]-[C:3].[O;H0;D1;+0:4]=[CH;D2;+0:5]-[c:6](:[c:7]):[c:8]>>[C:3]-[C:2]-[CH2;D2;+0:1]-[CH;D3;+0:5](-[OH;D1;+0:4])-[c:6](:[c:7]):[c:8] | null | [] | null | null | 2 | HOUR | A solution of 20.0 g of 3-phenylpropyl bromide in 300 ml of ether is treated at -60° while stirring within 15 minutes with a solution of 71.8 ml of tert.butyllithium (1.4 molar) in pentane. After 10 minutes there is added dropwise at this temperature within 15 minutes a solution of 22.14 g of vanillin benzyl ether in 2... | 10.6084/m9.figshare.5104873.v1 | null | Primary halide.Aldehyde | Secondary alcohol | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | Br- | CCOCC.CCCCC | null | 2 | BrCCCc1ccccc1.COc1cc(C=O)ccc1OCc1ccccc1>CCOCC.CCCCC>COc1cc(C(O)CCCc2ccccc2)ccc1OCc1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-04c16c9f6b5842da813810d2c8169fd5 | COc1cc(C(O)CCCc2ccccc2)ccc1OCc1ccccc1>>COc1cc(C(=O)CCCc2ccccc2)ccc1OCc1ccccc1 | C(C1=CC=CC=C1)OC1=C(C=C(C(CCCC2=CC=CC=C2)O)C=C1)OC>>C(C1=CC=CC=C1)OC1=C(C=C(C=C1)C(CCCC1=CC=CC=C1)=O)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]([OH:7])[CH2:8][CH2:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17][cH:18][c:19]1[O:20][CH2:21][c:22]1[cH:23][cH:24][cH:25][cH:26][cH:27]1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[CH2:8][CH2:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17][cH:18][c:19]1... | COc1cc(C(O)CCCc2ccccc2)ccc1OCc1ccccc1 | COc1cc(C(=O)CCCc2ccccc2)ccc1OCc1ccccc1 | null | [O-2].[O-2].[Mn+4] | C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | c7c20d2959ac48847b03cc1265962cf99a8ec8a85900c087dabb30077298c66c | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | O=C(CCCc1ccccc1)c1ccc(OCc2ccccc2)cc1 | [C:1]-[C:2]-[CH;D3;+0:3](-[OH;D1;+0:4])-[c:5](:[c:6]):[c:7]>>[C:1]-[C:2]-[C;H0;D3;+0:3](=[O;H0;D1;+0:4])-[c:5](:[c:6]):[c:7] | null | [] | null | null | 2 | HOUR | A solution of 9.0 g of 4-(benzyloxy)-3-methoxy-α-(3-phenylpropyl)benzyl alcohol in 250 ml of methylene chloride is treated with 90 g of manganese dioxide and held at the reflux temperature for 2 hours. After cooling, the precipitate is filtered under suction and washed with methylene chloride. The filtrate is evaporate... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | null | null | c1ccccc1.c1ccccc1.c1ccccc1 | null | [O-2].[O-2].[Mn+4].C(Cl)Cl | null | 2 | COc1cc(C(O)CCCc2ccccc2)ccc1OCc1ccccc1>[O-2].[O-2].[Mn+4].C(Cl)Cl>COc1cc(C(=O)CCCc2ccccc2)ccc1OCc1ccccc1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-62a4bf076f784ce68c20fd43fb23cb1b | COc1cc(C(=O)CCCc2ccccc2)ccc1OCc1ccccc1>>COc1cc(C(=O)CCCc2ccccc2)ccc1O | CCCCCC.C(C1=CC=CC=C1)OC1=C(C=C(C=C1)C(CCCC1=CC=CC=C1)=O)OC.N>>OC1=C(C=C(C=C1)C(CCCC1=CC=CC=C1)=O)OC | c1ccc(C[O:20][c:19]2[c:3]([O:2][CH3:1])[cH:4][c:5]([C:6](=[O:7])[CH2:8][CH2:9][CH2:10][c:11]3[cH:12][cH:13][cH:14][cH:15][cH:16]3)[cH:17][cH:18]2)cc1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[CH2:8][CH2:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17][cH:18][c:19]1[OH:20] | COc1cc(C(=O)CCCc2ccccc2)ccc1OCc1ccccc1 | COc1cc(C(=O)CCCc2ccccc2)ccc1O | null | null | CCOCC.C(C)(=O)O.Br | Deprotection | Hydroxyl benzyl deprotection | 36869d1fe85185a14d9eb30bf05178c600a9b6eca277ffaf3803578c30e0bf5d | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C(CCCc1ccccc1)c1ccccc1 | [c:1]:[c:2](-[O;H0;D2;+0:3]-C-c1:c:c:c:c:c:1):[c:4]>>[OH;D1;+0:3]-[c:2](:[c:1]):[c:4] | null | [] | null | null | null | null | A solution of 7.0 g of 4'-(benzyloxy)-3'-methoxy-4-phenylbutyrophenone in 40 ml of 33 percent hydrobromic acid in glacial acetic acid is stirred at room temperature for 5 hours and subsequently poured into 500 ml of ice-water. The solution is adjusted to pH 6.0 by the addition of conc. ammonia and extracted three times... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | c1ccccc1 | null | c1ccccc1.c1ccccc1 | Other | CCOCC.C(C)(=O)O.Br | null | null | COc1cc(C(=O)CCCc2ccccc2)ccc1OCc1ccccc1>CCOCC.C(C)(=O)O.Br>COc1cc(C(=O)CCCc2ccccc2)ccc1O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-2de9873996044fb8a14c659c901f4b0f | COc1cc(C(=O)CCCc2ccccc2)ccc1O.O=[N+]([O-])O>>COc1cc(C(=O)CCCc2ccccc2)cc([N+](=O)[O-])c1O | [N+](=O)(O)[O-].OC1=C(C=C(C=C1)C(CCCC1=CC=CC=C1)=O)OC>>OC1=C(C=C(C=C1[N+](=O)[O-])C(CCCC1=CC=CC=C1)=O)OC | [CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[CH2:8][CH2:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17][cH:18][c:22]1[OH:23].O[N+:19](=[O:20])[O-:21]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[CH2:8][CH2:9][CH2:10][c:11]2[cH:12][cH:13][cH:14][cH:15][cH:16]2)[cH:17][c:18]([N+:19](=[O:20])[O-:21])[c:22]1[O... | COc1cc(C(=O)CCCc2ccccc2)ccc1O.O=[N+]([O-])O | COc1cc(C(=O)CCCc2ccccc2)cc([N+](=O)[O-])c1O | null | null | C(C)(=O)O.C(C)(=O)OCC | Functional Group Addition | Aromatic nitration with HNO3 | 53848b8b2bb4e867226e49db2e60519b24be9379900e3ad7c56af54fe8fde7a5 | ddce49825c02b8965f10c8d99e3c841d26e1f136da6037b417c09313e6d73097 | O=C(CCCc1ccccc1)c1ccccc1 | O-[N+;H0;D3:1](-[O;-;D1;H0:2])=[O;D1;H0:3].[O;D1;H0:4]=[C:5]-[c:6]:[c:7]:[cH;D2;+0:8]:[c:9](-[O;D1;H1:10]):[c:11]>>[O;-;D1;H0:2]-[N+;H0;D3:1](=[O;D1;H0:3])-[c;H0;D3;+0:8](:[c:7]:[c:6]-[C:5]=[O;D1;H0:4]):[c:9](-[O;D1;H1:10]):[c:11] | null | [] | null | null | 2 | HOUR | A solution of 0.79 ml of 65 percent nitric acid in 25 ml of glacial acetic acid is added dropwise to a solution of 2.2 g of 4'-hydroxy-3'-methoxy-4- phenylbutyrophenone in 25 ml of glacial acetic acid and the mixture is stirred at room temperature for an additional 2 hours. The mixture is poured into 150 ml of ice-wate... | 10.6084/m9.figshare.5104873.v1 | null | Nitrate | Nitro group | c1ccccc1 | c1ccccc1 | c1ccccc1.c1ccccc1 | HO- | C(C)(=O)O.C(C)(=O)OCC | null | 2 | COc1cc(C(=O)CCCc2ccccc2)ccc1O.O=[N+]([O-])O>C(C)(=O)O.C(C)(=O)OCC>COc1cc(C(=O)CCCc2ccccc2)cc([N+](=O)[O-])c1O |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-cd7705cd929d4bd195817486d6d7ead7 | COc1cc(C(=O)CCCc2ccccc2)cc([N+](=O)[O-])c1O>>O=C(CCCc1ccccc1)c1cc(O)c(O)c([N+](=O)[O-])c1 | OC1=C(C=C(C=C1[N+](=O)[O-])C(CCCC1=CC=CC=C1)=O)OC.Cl.N1=CC=CC=C1>>OC=1C=C(C=C(C1O)[N+](=O)[O-])C(CCCC1=CC=CC=C1)=O | C[O:15][c:14]1[cH:13][c:12]([C:2](=[O:1])[CH2:3][CH2:4][CH2:5][c:6]2[cH:7][cH:8][cH:9][cH:10][cH:11]2)[cH:22][c:18]([N+:19](=[O:20])[O-:21])[c:16]1[OH:17]>>[O:1]=[C:2]([CH2:3][CH2:4][CH2:5][c:6]1[cH:7][cH:8][cH:9][cH:10][cH:11]1)[c:12]1[cH:13][c:14]([OH:15])[c:16]([OH:17])[c:18]([N+:19](=[O:20])[O-:21])[cH:22]1 | COc1cc(C(=O)CCCc2ccccc2)cc([N+](=O)[O-])c1O | O=C(CCCc1ccccc1)c1cc(O)c(O)c([N+](=O)[O-])c1 | null | null | null | Deprotection | Cleavage of methoxy ethers to alcohols | c5320c7dfa4f544d4900efcae9b3262bf0d5286bcf39c86109232351f35b23d5 | 26a36596df80ec137b0e8087297418351c93c32819177f680675220622f215d4 | O=C(CCCc1ccccc1)c1ccccc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4] | null | [] | null | null | null | null | 1.0 g of 4'-hydroxy-3'-methoxy-5'-nitro-4-phenylbutyrophenone is held at 200° for 1 hour with 8 g of pyridine hydrochloride. The reaction mixture is poured while still warm into ice-water and extracted with ethyl acetate. The organic phase is washed with 1N hydrochloric acid and subsequently with water, dried over sodi... | 10.6084/m9.figshare.5104873.v1 | null | Ether | Aromatic alcohol | null | null | c1ccccc1.c1ccccc1 | Other | null | null | null | COc1cc(C(=O)CCCc2ccccc2)cc([N+](=O)[O-])c1O>>O=C(CCCc1ccccc1)c1cc(O)c(O)c([N+](=O)[O-])c1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-801e03e84b904b0eaff29e379d9b3de0 | C#N.COc1cc(C=O)cc([N+](=O)[O-])c1OC>>COc1ccc(C(O)C#N)cc1OC | C#N.[C-]#N.[K+].COC=1C=C(C=O)C=C(C1OC)[N+](=O)[O-].Cl>>OC(C#N)C1=CC(=C(C=C1)OC)OC | [CH:9]#[N:10].O=[N+]([O-])[c:11]1[cH:5][c:6]([CH:7]=[O:8])[cH:4][c:3]([O:2][CH3:1])[c:12]1[O:13][CH3:14]>>[CH3:1][O:2][c:3]1[cH:4][cH:5][c:6]([CH:7]([OH:8])[C:9]#[N:10])[cH:11][c:12]1[O:13][CH3:14] | C#N.COc1cc(C=O)cc([N+](=O)[O-])c1OC | COc1ccc(C(O)C#N)cc1OC | null | null | O1CCOCC1.O.CCOCC | Functional Group Interconversion | OtherReaction | dedb3320a9c642061429f9f1145e2e2f9151398412253972f27824f5d20920c4 | b6046f26583e37283e869a898b0c2ff5184c6f76bf805e57d099b3e31a2529fe | c1ccccc1 | O=[N+](-[O-])-[c;H0;D3;+0:1]1:[cH;D2;+0:2]:[c;H0;D3;+0:3](-[CH;D2;+0:4]=[O;H0;D1;+0:5]):[cH;D2;+0:6]:[c:7](-[#8:8]):[c:9]:1-[#8:10].[CH;D1;+0:11]#[N;D1;H0:12]>>[#8:10]-[c:9]1:[cH;D2;+0:1]:[c;H0;D3;+0:3](-[CH;D3;+0:4](-[OH;D1;+0:5])-[C;H0;D2;+0:11]#[N;D1;H0:12]):[cH;D2;+0:2]:[cH;D2;+0:6]:[c:7]:1-[#8:8] | null | [] | null | null | 30 | MINUTE | A solution of 14.68 g of potassium cyanide in 20 ml of water is added to a solution of 10.0 g of 3,4-dimethoxy-5-nitrobenzaldehyde in 100 ml of dioxane. 18.81 ml of 37 percent hydrochloric acid are now added dropwise thereto within 30 minutes while stirring vigorously. After the addition of 120 ml of ether, the excess ... | 10.6084/m9.figshare.5104873.v1 | null | Aldehyde.Nitrile.Nitro group | Nitrile.Secondary alcohol | c1ccccc1 | c1ccccc1 | c1ccccc1 | Other | O1CCOCC1.O.CCOCC | null | 0.5 | C#N.COc1cc(C=O)cc([N+](=O)[O-])c1OC>O1CCOCC1.O.CCOCC>COc1ccc(C(O)C#N)cc1OC |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-030e0caa3c5b4b03bb432d63d84e972a | CCOC(=N)C(O)c1cc(OC)c(OC)c([N+](=O)[O-])c1.Nc1ccccc1N>>COc1cc(C(O)c2nc3ccccc3[nH]2)cc([N+](=O)[O-])c1OC | COC=1C=C(C=C(C1OC)[N+](=O)[O-])C(C(OCC)=N)O.C1(=C(C=CC=C1)N)N>>COC=1C=C(C=C(C1OC)[N+](=O)[O-])C(O)C=1NC2=C(N1)C=CC=C2 | CCO[C:8]([CH:6]([c:5]1[cH:4][c:3]([O:2][CH3:1])[c:22]([O:23][CH3:24])[c:18]([N+:19](=[O:20])[O-:21])[cH:17]1)[OH:7])=[NH:9].N[c:10]1[cH:11][cH:12][cH:13][cH:14][c:15]1[NH2:16]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]([OH:7])[c:8]2[n:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[nH:16]2)[cH:17][c:18]([N+:19](=[O:20])[O-:21]... | CCOC(=N)C(O)c1cc(OC)c(OC)c([N+](=O)[O-])c1.Nc1ccccc1N | COc1cc(C(O)c2nc3ccccc3[nH]2)cc([N+](=O)[O-])c1OC | null | null | C(C)O | Aromatic Heterocycle Formation | OtherReaction | c6f18837f1f329335b64588a1d396acd44640ce7ca3e5fb6561574880d148f3a | f234cabe9d1f15bf4e86910dc4bc24e5f2e0626e524ea2c3289a1403a01f49e2 | c1ccc(Cc2nc3ccccc3[nH]2)cc1 | C-C-O-[C;H0;D3;+0:1](=[NH;D1;+0:2])-[C:3](-[O;D1;H1:4])-[c:5].N-[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](-[NH2;D1;+0:10]):[c:11]>>[O;D1;H1:4]-[C:3](-[c:5])-[c;H0;D3;+0:1]1:[n;H0;D2;+0:2]:[c;H0;D3;+0:6](:[c:7]:[c:8]):[c:9](:[c:11]):[nH;D2;+0:10]:1 | null | [] | null | null | 2 | HOUR | 19.7 g of ethyl (3,4-dimethoxy-5-nitrophenyl)hydroxyacetimidate are dissolved in 500 ml of ethanol. 6.73 g of o-phenylenediamine are added, the mixture is stirred at room temperature for 2 hours and subsequently held at the reflux temperature overnight. After distillation of the solvent, the residue is treated with 50 ... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Primary amine.Primary amine | null | c1ccccc1 | c1ccc2[nH]cnc2c1 | c1ccccc1.c1ccc2[nH]cnc2c1 | HO- | C(C)O | null | 2 | CCOC(=N)C(O)c1cc(OC)c(OC)c([N+](=O)[O-])c1.Nc1ccccc1N>C(C)O>COc1cc(C(O)c2nc3ccccc3[nH]2)cc([N+](=O)[O-])c1OC |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-b6049a0e1e50493580cda486cdbf10d0 | COc1cc(C(O)c2nc3ccccc3[nH]2)cc([N+](=O)[O-])c1OC>>COc1cc(C(=O)c2nc3ccccc3[nH]2)cc([N+](=O)[O-])c1OC | COC=1C=C(C=C(C1OC)[N+](=O)[O-])C(O)C=1NC2=C(N1)C=CC=C2>>COC=1C=C(C=C(C1OC)[N+](=O)[O-])C(=O)C=1NC2=C(N1)C=CC=C2 | [CH3:1][O:2][c:3]1[cH:4][c:5]([CH:6]([OH:7])[c:8]2[n:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[nH:16]2)[cH:17][c:18]([N+:19](=[O:20])[O-:21])[c:22]1[O:23][CH3:24]>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[c:8]2[n:9][c:10]3[cH:11][cH:12][cH:13][cH:14][c:15]3[nH:16]2)[cH:17][c:18]([N+:19](=[O:20])[O-:21])[c:22]1[O:... | COc1cc(C(O)c2nc3ccccc3[nH]2)cc([N+](=O)[O-])c1OC | COc1cc(C(=O)c2nc3ccccc3[nH]2)cc([N+](=O)[O-])c1OC | null | [O-2].[O-2].[Mn+4] | C(Cl)Cl | Oxidation | Oxidation or Dehydrogenation of Alcohols to Aldehydes and Ketones | c7c20d2959ac48847b03cc1265962cf99a8ec8a85900c087dabb30077298c66c | 767cfd93f5821ebb9e1e72addd9cb404b20b0c821d246ae6b87a5776b74a455b | O=C(c1ccccc1)c1nc2ccccc2[nH]1 | [OH;D1;+0:1]-[CH;D3;+0:2](-[c:3](:[c:4]):[c:5])-[c:6]1:[#7;a:7]:[c:8]:[c:9]:[#7;a:10]:1>>[O;H0;D1;+0:1]=[C;H0;D3;+0:2](-[c:3](:[c:4]):[c:5])-[c:6]1:[#7;a:7]:[c:8]:[c:9]:[#7;a:10]:1 | null | [] | null | null | null | null | 13.2 g of α-(3,4-dimethoxy-5-nitrophenyl)-2-benzimidazolemethanol are dissolved in 200 ml of methylene chloride and, after treatment with 130 g of manganese dioxide, the mixture is stirred at the reflux temperature for 2 hours. After filtration, the solvent is distilled. There is obtained 2-benzimidazolyl (3,4-dimethox... | 10.6084/m9.figshare.5104873.v1 | null | Secondary alcohol | Ketone | null | null | c1ccccc1.c1ccc2[nH]cnc2c1 | null | [O-2].[O-2].[Mn+4].C(Cl)Cl | null | null | COc1cc(C(O)c2nc3ccccc3[nH]2)cc([N+](=O)[O-])c1OC>[O-2].[O-2].[Mn+4].C(Cl)Cl>COc1cc(C(=O)c2nc3ccccc3[nH]2)cc([N+](=O)[O-])c1OC |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-ca378bffe04e423fa1b4aa032a117d2e | COc1cc(C(=O)c2nc3ccccc3[nH]2)cc([N+](=O)[O-])c1OC>>O=C(c1cc(O)c(O)c([N+](=O)[O-])c1)c1nc2ccccc2[nH]1 | COC=1C=C(C=C(C1OC)[N+](=O)[O-])C(=O)C=1NC2=C(N1)C=CC=C2.Cl.N1=CC=CC=C1>>OC=1C=C(C=C(C1O)[N+](=O)[O-])C(=O)C=1NC2=C(N1)C=CC=C2 | C[O:6][c:5]1[cH:4][c:3]([C:2](=[O:1])[c:14]2[n:15][c:16]3[cH:17][cH:18][cH:19][cH:20][c:21]3[nH:22]2)[cH:13][c:9]([N+:10](=[O:11])[O-:12])[c:7]1[O:8]C>>[O:1]=[C:2]([c:3]1[cH:4][c:5]([OH:6])[c:7]([OH:8])[c:9]([N+:10](=[O:11])[O-:12])[cH:13]1)[c:14]1[n:15][c:16]2[cH:17][cH:18][cH:19][cH:20][c:21]2[nH:22]1 | COc1cc(C(=O)c2nc3ccccc3[nH]2)cc([N+](=O)[O-])c1OC | O=C(c1cc(O)c(O)c([N+](=O)[O-])c1)c1nc2ccccc2[nH]1 | null | null | null | Deprotection | OtherReaction | a0f05885bbc65ae2846cad0ac34029941211b2ef3a426958b0c8aa83bb16fe86 | 9df751cd682ad9d54ed75d7313aaead6a019c5d37ede15c4672866d319b900ff | O=C(c1ccccc1)c1nc2ccccc2[nH]1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4](-[O;H0;D2;+0:5]-C):[c:6]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4](-[OH;D1;+0:5]):[c:6] | null | [] | null | null | null | null | 1.0 g of 2-benzimidazolyl (3,4-dimethoxy- 5-nitrophenyl) ketone and 8.0 g of pyridine hydrochloride are held at 200° for 60 minutes. The dark solution is poured while still warm into ice-water and extracted three times with 100 ml of ethyl acetate each time. The organic phase is washed with water, dried over sodium sul... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aromatic alcohol.Aromatic alcohol | null | null | c1ccccc1.c1ccc2[nH]cnc2c1 | Other | null | null | null | COc1cc(C(=O)c2nc3ccccc3[nH]2)cc([N+](=O)[O-])c1OC>>O=C(c1cc(O)c(O)c([N+](=O)[O-])c1)c1nc2ccccc2[nH]1 |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-9c8ea385d239420da9833029a29b5b54 | CC(N)=NO.COc1cc(C(=O)n2ccnc2)cc([N+](=O)[O-])c1OC>>COc1cc(C(=O)ON=C(C)N)cc([N+](=O)[O-])c1OC | COC=1C=C(C(=O)N2C=NC=C2)C=C(C1OC)[N+](=O)[O-].C(C)(N)=NO>>COC=1C=C(C(=O)ON=C(C)N)C=C(C1OC)[N+](=O)[O-] | [OH:8][N:9]=[C:10]([CH3:11])[NH2:12].c1cn([C:6]([c:5]2[cH:4][c:3]([O:2][CH3:1])[c:18]([O:19][CH3:20])[c:14]([N+:15](=[O:16])[O-:17])[cH:13]2)=[O:7])cn1>>[CH3:1][O:2][c:3]1[cH:4][c:5]([C:6](=[O:7])[O:8][N:9]=[C:10]([CH3:11])[NH2:12])[cH:13][c:14]([N+:15](=[O:16])[O-:17])[c:18]1[O:19][CH3:20] | CC(N)=NO.COc1cc(C(=O)n2ccnc2)cc([N+](=O)[O-])c1OC | COc1cc(C(=O)ON=C(C)N)cc([N+](=O)[O-])c1OC | null | null | CN(C=O)C | Acylation | OtherReaction | 2c784cdc1a424c081af1dd85835bb592467da92d12b431740c77ce9e7f80a2e1 | 368202c745ffcdbd810e9756494c2940d48361bbcf0f17c6c2afef06f7c8a1a1 | c1ccccc1 | [C;D1;H3:1]-[C:2](-[N;D1;H2:3])=[#7:4]-[OH;D1;+0:5].[O;D1;H0:6]=[C;H0;D3;+0:7](-[c:8](:[c:9]):[c:10])-n1:c:c:n:c:1>>[C;D1;H3:1]-[C:2](-[N;D1;H2:3])=[#7:4]-[O;H0;D2;+0:5]-[C;H0;D3;+0:7](=[O;D1;H0:6])-[c:8](:[c:9]):[c:10] | null | [] | null | null | 1 | HOUR | 10.0 g of 1-(3,4-dimethoxy-5-nitrobenzoyl)imidazole in 50 ml of dimethylformamide are treated with 6.95 g of acetamidoxime, whereupon the mixture is stirred at 70° for 1 hour. After cooling, the mixture is poured into 500 ml of ice-water and stirred for 30 minutes. The separated crystals are filtered under suction and ... | 10.6084/m9.figshare.5104873.v1 | null | Oxime | null | c1c[nH]cn1 | null | c1ccccc1 | Other | CN(C=O)C | null | 1 | CC(N)=NO.COc1cc(C(=O)n2ccnc2)cc([N+](=O)[O-])c1OC>CN(C=O)C>COc1cc(C(=O)ON=C(C)N)cc([N+](=O)[O-])c1OC |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-f347339a177f4ab8a08748288e49560e | COc1cc(C(=O)ON=C(C)N)cc([N+](=O)[O-])c1OC>>COc1cc(-c2nc(C)no2)cc([N+](=O)[O-])c1OC | COC=1C=C(C(=O)ON=C(C)N)C=C(C1OC)[N+](=O)[O-]>>COC=1C=C(C=C(C1OC)[N+](=O)[O-])C1=NC(=NO1)C | O=[C:6]([c:5]1[cH:4][c:3]([O:2][CH3:1])[c:17]([O:18][CH3:19])[c:13]([N+:14](=[O:15])[O-:16])[cH:12]1)[O:11][N:10]=[C:8]([NH2:7])[CH3:9]>>[CH3:1][O:2][c:3]1[cH:4][c:5](-[c:6]2[n:7][c:8]([CH3:9])[n:10][o:11]2)[cH:12][c:13]([N+:14](=[O:15])[O-:16])[c:17]1[O:18][CH3:19] | COc1cc(C(=O)ON=C(C)N)cc([N+](=O)[O-])c1OC | COc1cc(-c2nc(C)no2)cc([N+](=O)[O-])c1OC | null | null | C(C)(=O)O | Aromatic Heterocycle Formation | OtherReaction | 8f6e9accb2c920efc1b398f875c8391bc3c0547be37e5059f4768e69cc3d00d5 | 0c2e6cfe0bdb8f8cd78303a7637b3ef339f807f5bc27c4a22ad516ce20b37476 | c1ccc(-c2ncno2)cc1 | O=[C;H0;D3;+0:1](-[O;H0;D2;+0:2]-[N;H0;D2;+0:3]=[C;H0;D3;+0:4](-[C;D1;H3:5])-[NH2;D1;+0:6])-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]>>[C;D1;H3:5]-[c;H0;D3;+0:4]1:[n;H0;D2;+0:3]:[o;H0;D2;+0:2]:[c;H0;D3;+0:1](-[c;H0;D3;+0:7](:[c:8]:[c:9]):[c:10]:[c:11]):[n;H0;D2;+0:6]:1 | null | [] | null | null | null | null | 2.0 g of N'-[(3,4-dimethoxy-5-nitrobenzoyl)oxy] acetamidine are held at reflux temperature for 1 hour in 20 ml of glacial acetic acid. After distillation of the acetic acid, the crystalline residue is recrystallized from ether/hexane. There is obtained 5-(3,4-dimethoxy-5-nitrophenyl)-3-methyl-1,2,4-oxadiazole in the fo... | 10.6084/m9.figshare.5104873.v1 | null | Primary amine | null | null | c1ncon1 | c1ccccc1.c1ncon1 | HO- | C(C)(=O)O | null | null | COc1cc(C(=O)ON=C(C)N)cc([N+](=O)[O-])c1OC>C(C)(=O)O>COc1cc(-c2nc(C)no2)cc([N+](=O)[O-])c1OC |
ord_dataset-c2ad1656a3ca4d08888ffb6e3f3a2742 | ord-3cf89a74dec1451980ee81dfbefe3083 | COc1cc(-c2nc(C)no2)cc([N+](=O)[O-])c1OC>>Cc1noc(-c2cc(O)c(O)c([N+](=O)[O-])c2)n1 | COC=1C=C(C=C(C1OC)[N+](=O)[O-])C1=NC(=NO1)C.B(Br)(Br)Br.C(C)O>>CC1=NOC(=N1)C1=CC(=C(C(O)=C1)O)[N+](=O)[O-] | C[O:9][c:8]1[cH:7][c:6](-[c:5]2[o:4][n:3][c:2]([CH3:1])[n:17]2)[cH:16][c:12]([N+:13](=[O:14])[O-:15])[c:10]1[O:11]C>>[CH3:1][c:2]1[n:3][o:4][c:5](-[c:6]2[cH:7][c:8]([OH:9])[c:10]([OH:11])[c:12]([N+:13](=[O:14])[O-:15])[cH:16]2)[n:17]1 | COc1cc(-c2nc(C)no2)cc([N+](=O)[O-])c1OC | Cc1noc(-c2cc(O)c(O)c([N+](=O)[O-])c2)n1 | null | null | C(Cl)Cl | Deprotection | OtherReaction | a0f05885bbc65ae2846cad0ac34029941211b2ef3a426958b0c8aa83bb16fe86 | 9df751cd682ad9d54ed75d7313aaead6a019c5d37ede15c4672866d319b900ff | c1ccc(-c2ncno2)cc1 | C-[O;H0;D2;+0:1]-[c:2](:[c:3]):[c:4](-[O;H0;D2;+0:5]-C):[c:6]>>[OH;D1;+0:1]-[c:2](:[c:3]):[c:4](-[OH;D1;+0:5]):[c:6] | null | [] | null | null | 48 | HOUR | 2.5 g of 5-(3,4-dimethoxy-5-nitrophenyl)-3-methyl-1,2,4-oxadiazole are dissolved in 70 ml of methylene chloride. After cooling to -60° there is added dropwise thereto within 20 minutes while stirring a solution of 23.62 g of boron tribromide in 50 ml of methylene chloride, whereupon the mixture is held at the reflux te... | 10.6084/m9.figshare.5104873.v1 | null | Ether.Ether | Aromatic alcohol.Aromatic alcohol | null | null | c1ncon1.c1ccccc1 | Other | C(Cl)Cl | null | 48 | COc1cc(-c2nc(C)no2)cc([N+](=O)[O-])c1OC>C(Cl)Cl>Cc1noc(-c2cc(O)c(O)c([N+](=O)[O-])c2)n1 |
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