Oxidation of 3-aminopyridine (II) with 30% hydrogen peroxide and conc. sulfuric acid, at room temperature, results in the formation of 3, 3′-azoxypyridine (III) and not the anticipated 3-nitropyridine (I).
Derivation of 3, 5-dinitro-4-hydroxypyridine (IV) to its 4-chloro compound (V) by treatment with phosphoryl chloride and application of anhydrous hydrazine to (V) afforded 3, 5-dinitro-4-pyridylhydrazine (VI) as needle crystals, mp 161.5°. Heating of (VI) with silver acetate at 135-140° finally afforded 3, 5-dinitropyridine (VII), with a by-product of plate crystals melting at 168°, which was assumed to be 3-amino-5-nitropyridine.