N-Phenylanthranilic Acid → 5-Chloro-3-hydroxy-1-phenyl-1H-indole-2-carboxylic acid methyl ester

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[N:6]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:7]2[C:12]([C:13]=1[OH:14])=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:4].[Cl:21]C1C=CC(NC2C=CC=CC=2)=C(C=1)C(O)=O.C1(NC2C=CC=CC=2C(O)=O)C=CC=CC=1>>[CH3:1][O:2][C:3]([C:5]1[N:6]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:7]2[C:12]([C:13]=1[OH:14])=[CH:11][C:10]([Cl:21])=[CH:9][CH:8]=2)=[O:4]

Participants

Reactant 3

HCID 4386N-Phenylanthranilic Acid

HCID 123694565-Chloro-2-(phenylamino)benzoic acid

HCID 54687160Methyl 3-hydroxy-1-phenyl-1H-indole-2-carboxylate

Product 1

HCID 547342815-Chloro-3-hydroxy-1-phenyl-1H-indole-2-carboxylic acid methyl ester

Procedure

Prepared in a manner analogous to the multistep procedure described [P. Friedlander and K. Kunz, Chem. Ber., 55, 1597 (1922)] for the preparation of 3-hydroxy-1-phenyl-1H-indole-2-carboxylic acid methyl ester, with 5-chloro-2-(phenylamino)benzoic acid substituted for 2-(phenylamino)benzoic acid in the first step of the synthetic sequence. The final indole product was recrystallized from aqueous 2-methoxyethanol to yield analytically pure product, mp 170°-173° C.