Reaction of freshly prepared o-aminobenzaldehyde (2) 6 with a substituted acetone (1) and 33% KOH in refluxing ethanol afforded 3-phenyl-and 3-methoxyquinaldine (3a and 3b) in 81% and 76% yields respectively. Our initial attempts to perform this condensation using a catalytic amount of acetic acid resulted in a low yield of 3-phenylquinaldine (24%), whereas a similar reaction to prepare 3-methoxyquinaldine gave a complex mixture of products ...
