P-Anisidine → 6-Chloro-2-(4-methoxyanilino)-3-nitrobenzoic acid

Participants

Reaction Conditions

Reaction Steps

To 74 g (0.60 mol) of p-anisidine stirred mechanically at 75° C. was added 35.4 g (0.15 mol) of 2,6-dichloro-3-nitrobenzoic acid [Lehmstedt and Schrader, Berichte 70B, 1526 (1937)] in small portions over one-half hour. The mixture was heated at 75° C. for 24 hours with stirring during the first two hours. The reaction mixture was cooled and the resulting solid mass was triturated in a mechanical blender with 300 ml of 2.4N hydrochloric acid. The solid was collected, washed with 3N hydrochloric acid, stirred in 400 ml of 0.5N sodium carbonate, and filtered. The filtrate, diluted with 250 ml of water, was gradually acidified with 4N hydrochloric acid. The precipitate was collected, washed with water, and dried to provide 38.5 g (79%) of the red title compound, mp 205°-213° C. A purified sample, from toluene, melts at 212°-215° C.

Provenance & Evidence