Synthesis and reduction of N-substituted 5-nitrosoquinolin-8-amines

Abstract

N-Substituted 5-nitrosoquinolin-8-amines were synthesized for the first time by amination of 5-nitrosoquinolin-8-ol with primary aliphatic amines. The amination of 5-nitrosoquinolin-8-ol with hexamethylenediamine afforded N¹,N⁶-bis(5-nitrosoquinolin-8-yl)hexane-1,6-diamine. The resulting nitrosoquinolinamines were reduced with hydrazine hydrate over Pd/C to N⁸-alkylquinoline-5,8-diamines and N¹,N⁶-bis-(5-aminoquinolin-8-yl)hexane-1,6-diamine.