5-Hydroxy-2-alkylpyridines (VII) were prepared by a sequence of reactions starting with the malonation of 2-chloro-5-nitropyridine with diethyl alkylmalonates. Malonation failed with 4-methoxy-3-nitropyridine (VIII) and 2-chloro-3-nitropyridine (XII), yielding decomposition products only. Reactivity of the. methoxyl groups in 4-methoxy-3-nitropyridine (VIII) and in 2-methoxy-3-nitropyridine (XV) was compared with respect to the rearrangement to N-methylpyridone, the reaction with aromatic amines, and hydrolysis with dilute acids. Methylation of 2-hydroxy-3-nitropyridine yields either 2-methoxy-3-nitropyridine (XV) or N-methyl-3-nitro-2-pyridone (XVI) as can be expected.