Abstract
A new synthetic process is described for building up the pyridine ring by the utilization of an active methyl group and a carboxyl adjacent to it in the pyridine ring. The reaction of ethyl 2-methylnicotinate and formaldehyde (or acetaldehyde) gave a lactone which was led to an amide, and its oxidation gave 5-hydroxy-1, 6-naphthyridine. 1, 6-Naphthyridine and 7-methyl-1, 6-naphthyridine were synthesized from their 5-hydroxy derivatives via the chloro and hydrazino compounds. Methyl-1, 6-naphthyridine N-oxide obtained by the Skraup reaction of 4-amino-2-picoline 1-oxide was established as the 5-methyl derivative.
