Evidence is presented, based on 15N-labeling experiments and'H NMR spectroscopy, that the conversion of 2-chloro-5-nitropyridine (1) into 2-amino-5-nitropyridine by treatment with potassium amide/liquid ammonia proceeds to about 75% according to a sequence of reactions involving addition of the amide ion to C-6, ring-opening, and ring-closure [S,(ANRORC) mechanism]. On the contrary, 2-chloro-3, 5-dinitropyridine (1 1) is nearly ...
