Organolithium chemistry of N-heterocycles. Part I. Action of phenyllithium on 2-methylpyridines and 2-methylquinolines

Abstract

Reaction of phenyl-lithium and 2-methylquinoline in diethyl ether gives, to the exclusion of azomethine addition, 90% side-chain metallation. Analogous compounds containing activated 2-methyl groups react similarly, except that 2,4-lutidine produced 2,4-dimethyl-6-phenylpyridine.