Regio- and Chemoselective Mono- and Bisnitration of 8-Amino quinoline Amides with Fe(NO 3 ) 3 ·9H 2 O as Promoter and Nitro Source.

An efficient and regioselective remote C(5)-H nitration of 8-aminoquinoline amides by using the economical and nontoxic Fe(NO3 )3 ·9H2 O as promoter and nitro source has been developed. Furthermore, when CuCl2 ·2H2 O was used as a catalyst, 8-aminoquinoline amides dominantly underwent bisnitration to give 5,7-dinitro-8-aminoquinoline amides. Notably, this is the first example in which Fe(NO3 )3 ·9H2 O plays a dual role as both chelating promoter and nitration reagent, and CuCl2 ·2H2 O acts as an efficient catalyst for the bisnitration of quinolines.