Hydrochloric Acid → Amino-5,6-dichloro-3-nitrobenzoic acid

Participants

Reaction Steps

To a stirred solution of 3-nitro-2,5,6-trichlorobenzoic acid (37.1 mmol, 10.0 g) in 150 mL of toluene, was added 2-chlorobenzylamine (81.6 mmol, 11.56 g). The reaction mixture was refluxed overnight, poured into dilute hydrochloric acid and vigorously stirred. The resulting solid was filtered. The product was dissolved in toluene and then precipitated with diethyl ether. Recrystallization of the product from methanol gave 3.4 g of 2-[2-chlorophenyl)methyl]amino-5,6-dichloro-3-nitrobenzoic acid; mp 168.5°-171° C.

Provenance & Evidence