Aromatic nucleophilic substitution reactions of 1-dialkylamino-2,4-dinitronaphthalene with primary or secondary amines in organic solvents: facile amine–amine exchange

Abstract

The dialkylamino group, (e.g., dimethyl-, diethyl-, and N-n-butyl-N-methylamino, piperidino, and pyrrolidino) of 1-dialkylamino-2,4-dinitronaphthalenes is rapidly replaced by primary amines, particularly in dimethyl sulphoxide; however, substitution does not occur for secondary amines except in the case of pyrrolidine.