ChemInform Abstract: Synthesis and Characterization of 4′-Amino and 4′-Nitro Derivatives of 4-N,N-Dimethylaminotriphenylmethane as Precursors for a Proximate Malachite Green Metabolite.

Abstract

Abstract This paper describes the preparation of 4′-amino ( 2 ) and 4′-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.