Hydrochloric Acid → 3-Methylsulfonyl-4-chloro-5-aminobenzoic acid

Participants

Reaction Conditions

Reaction Steps

A vigorously stirred mixture of iron powder (9.2 g.), ammonium chloride (880 mg.) water (27 ml.) and concentrated hydrochloric acid (0.1 ml.) is heated on a steam bath while 3-methylsulfonyl-4-chloro-5-nitrobenzoic acid (7.8 g.) is added in small portions during a one hour period. The reaction mixture is heated on a steam bath for 18 hours, cooled and filtered. The filter cake is suspended in water (75 ml.), basified with 10N sodium hydroxide, warmed to 50° C. and filtered. Acidification of the filtrate with hydrochloric acid gives pure 3-methylsulfonyl-4-chloro-5-aminobenzoic acid (4.3 g.; 62%) which melts at 277.5° C.

Provenance & Evidence