N-nitration of secondary amines with 4-chloro-5-methoxy-2-nitropyridazin-3-one

J Org Chem. 2003 Nov 14;68(23):9113-5. doi: 10.1021/jo0301503.

Abstract

N-Nitration of 4-chloro-5-substituted-pyridazin-3-one with copper nitrate trihydrate in acetic anhydride gave the corresponding 4-chloro-2-nitro-5-substituted-pyridazin-3-one. 4-Chloro-5-alkoxy-2-nitropyridazin-3-ones such as 5-methoxy (2b) and 5-ethoxy (2d) derivatives showed excellent nitro group transfer potentiality. N-Nitration of some secondary amines with 2b gave the corresponding N-nitramines under mild neutral condition in good yields.