Nucleophilic Substitution Reaction of 2,3,5,6-Tetrachloronitrobenzene with Primary and Secondary Amines under High Pressure

Abstract Nucleophilic substitution of 2,3,5,6-tetrachloronitrobenzene with secondary amines such as morpholine, piperidine, pyrrolidine, diethylamine, and ethylmethylamine, and primary amines such as aniline, benzylamine, butylamine, isobutylamine, s-butylamine, and t-butylamine, under high pressure of 0.6 GPa at 50 °C for 1—40 h in tetrahydrofuran gave nitro group substitution products together with ortho-mono-, meta-mono-, ortho-ortho-, and ortho-meta-dichloro substitution products. The ratio of these products depends on the bulkiness and amount of amines and the reaction conditions. The selectivity of the nitro group substitution and chlorine substitution depends mainly on the bulkiness of amines.