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An efficient and regioselective remote C(5)–H nitration of 8-aminoquinoline amides by using the economical and nontoxic Fe(NO 3 ) 3 ·9H 2 O as promoter and nitro source has been developed. Furthermore, when CuCl 2 ·2H 2 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(NO 3 ) 3 ·9H 2 O plays a dual role as both chelating promoter and nitration reagent, and CuCl 2 ·2H 2 O acts as an efficient catalyst for the bisnitration of quinolines.
He et al. (Fri,) studied this question.