N,N-Dimethylaniline → 3-Nitrobenzoic acid

Participants

Reaction Steps

A mixture of 28.0 g (0.20 mol) of p-phenetidine, 23.6 g (0.10 mol) of 2,6-dichloro-3-nitrobenzoic acid, and 80 ml of N,N-dimethylaniline was heated five hours on a steam bath. The resulting mixture was diluted with chloroform and extracted with 1N aq. NaOH. Acidification of the aqueous extract yielded 6-chloro-2-[4-ethoxyphenyl)amino]-3-nitrobenzoic acid as reddish brown crystals, mp 174°-176° C.

Provenance & Evidence