A study of the reaction of phenyllithium with 2-phenylquinoline

The reaction products of aryllithium compounds with 2-arylquinoline was restudied to expand the scope of the Gilman and Gainer synthesis of 2,2-phenyl-1,2-dihydroquinoline and 2-phenyl-2-p-tolyl-1,2-dihydroquinoline. In the study of the reaction, it was found that the reaction of 2-phenylquinoline with aryllithium actually produces several products as illustrated by modern separation techniques. We have shown that HPLC is a valid and improved approach for separating the several products not previously observed from this reaction. Thin Layer Chromatography has also shown the presence of the several products.