Anthranilic Acid → 2-Amino-4-methoxybenzoic acid

Reaction equation

[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[C:5]([N+:12]([O-])=O)[CH:4]=1.[NH4+].[OH-].C(O)(=O)C1C(=CC=CC=1)N>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH2:12])[C:6](=[CH:10][CH:11]=1)[C:7]([OH:9])=[O:8]

Participants

Reactant 3

HCID 227Anthranilic Acid

HCID 14923Ammonium Hydroxide

HCID 2886574-Methoxy-2-nitrobenzoic acid

Product 1

HCID 3510102-Amino-4-methoxybenzoic acid

Procedure

A solution of 4-methoxy-2-nitrobenzoic acid (19.3 g., 97.9 mmole) of 200 ml. 1 N NH4OH was reduced overnight in presence of 5% Pd/BaCO3. The reaction mixture was filtered and acidified with acetic acid to yield 15.8 g. (96%) of the anthranilic acid, M.P. 186°-188° C.