Ammonium Hydroxide → 2-Amino-3-chlorobenzoic acid

Reaction equation

S(S([O-])=O)([O-])=O.[Na+].[Na+].[Cl:9][C:10]1[C:11]([N+:19]([O-])=O)=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13]([OH:15])=[O:14].[OH-].[NH4+]>O>[Cl:9][C:10]1[C:11]([NH2:19])=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13]([OH:15])=[O:14]

Participants

Procedure

Sodium dithionite (104.4 g, 0.6 m) in water (400 ml) was added in portions to a slurry of 3-chloro-2-nitrobenzoic acid (30 g, 0.15 m) in water (200 ml) containing concentrated ammonium hydroxide solution (10 ml). After stirring an additional 20 minutes the mixture was filtered, acidified to pH 3-4 with concentrated hydrochloric acid and filtered again. The filtrate was saturated with sodium chloride and extracted with ether. Drying and concentration of the extract gave a white powder which was combined with the precipitates above. The crude product was used without further purification.