Acetic Acid → methyl 3-(2-methoxy-2-oxoethyl)-1H-indole-2-carboxylate
Reaction equation
[C:1]1([NH:7]N)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O=[C:10]([CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])[C:11]([O:13][CH3:14])=[O:12].C(O)(=O)C>CO>[CH3:20][O:19][C:17]([C:16]1[NH:7][C:1]2[C:6]([C:15]=1[CH2:10][C:11]([O:13][CH3:14])=[O:12])=[CH:5][CH:4]=[CH:3][CH:2]=2)=[O:18]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 75 °C
Procedure
Phenyl hydrazine (5.7 ml), dimethyl 2-oxoglutarate (10 g) and acetic acid (1.0 ml) in methanol (100 ml) were heated at reflux for 1 hour, then concentrated in in vacuo. The crude hydrazone (13 g) was dissolved in saturated methanolic hydrochloric acid (350 ml) and heated to 75° C. for 16 hours with continual stirring. The reaction was diluted with water (200 ml) and extracted with dichloromethane. Combined organic extracts were washed with saturated aqueous sodium hydrogencarbonate solution, water, saturated aqueous sodium chloride solution and dried (MgSO4). The solvent was removed in vacuo to give a yellow crystalline solid (7.0 g); NMR d (CD3SOCD3) 3.59 (s, 3H), 3.83 (s, 3H), 4.12 (s, 2H), 7.06 (t, 1H), 7.26 (t, 1H), 7.41 (d, 1H), 7.63 (d, 1H), 11.76 (brs, 1H); M/z (−) 246 (M−H+).
Workup
- temperatureat reflux for 1 hour
- concentrationconcentrated in in vacuo
- dissolutionThe crude hydrazone (13 g) was dissolved in saturated methanolic hydrochloric acid (350 ml)
- additionThe reaction was diluted with water (200 ml)
- extractionextracted with dichloromethane
- washCombined organic extracts were washed with saturated aqueous sodium hydrogencarbonate solution, water, saturated aqueous sodium chloride solution
- dry with materialdried (MgSO4)
- customThe solvent was removed in vacuo
Sources & evidence
- ORD record
- ord-5f8f7c4c721143ba9b148d60a787bbfe
- Source dataset
- uspto-grants-2004_12
- Patent number
- US06833387B1
Reaction notes
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