Ethyl 2-(2-cyanoanilino)acetate → Ethyl 3-amino-1H-indole-2-carboxylate

Reaction equation

[CH2:1]([O:3][C:4](=[O:15])[CH2:5][NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]#[N:14])[CH3:2].CC(C)([O-])C.[K+]>C1COCC1.[Cl-].[NH4+]>[NH2:14][C:13]1[C:8]2[C:7](=[CH:12][CH:11]=[CH:10][CH:9]=2)[NH:6][C:5]=1[C:4]([O:3][CH2:1][CH3:2])=[O:15]

Participants

Procedure

To a solution of N-(2-Cyanophenyl)glycine ethyl ester (8.1 g) in THF (125 mL) was added potassium t-butoxide (4.5 g) in one portion with stirring. After 10 min at room temperature the mixture was diluted with saturated ammonium chloride solution and the product was extracted with ether. After drying, over magnesium sulfate the solvent was removed in vacuo and the residue was recrystallized from 80% methanol to afford 3-Amino-2-carboethoxyindole as a tan solid.