Chlorination of the N-acetylnitronaphthylamines

Abstract

The chlorination of the N-acetyl derivatives of the fourteen possible nitronaphthylamines has been studied under a variety of conditons. Both substitution and addition processes occur; the latter have not been investigated in any detail. The reactivity and mode of substitution of the N-acetylnitronaphthylamines are compared to the behaviour of the parent naphthylamines, and also to other corresponding electrophilic substitutions. New compounds synthesised include thirteen mono- and di-chloronitronaphthylamines (and their acetyl derivatives), six diazonaphthols, and two tetrachloronaphthalenes.