Synthesis and characterization of 4\u27-amino and 4\u27-nitro derivatives of 4-N, N-dimethylaminotriphenylmethane as precursors for a proximate malachite green metabolite

This paper describes the preparation of 4\u27-amino (2) and 4\u27-nitro (3) derivatives of 4-N, N-dimethylaminotriphenylmethane as precursors for presumed DNA-binding metabolites of malachite green. The primary amine 2 was synthesized via a condensation of 4-lithiated bis-(N, N-trimethylsilyl)aniline and 4-(dimethylamino)benzophenone. A simple nitro-dediazoniation reaction of 2 failed to afford 3, but gave exclusively a mixture derived from hydro-dediazoniation followed by nitration and N-dealkylative-N-nitrosation. Direct nitration of N, N-dimethylaminotriphenylmethane, however, afforded 3 as well as other nitro isomers