We have revealed an anomalous reaction of 6-hydroxy-2, 2, 4-trimethyl-1, 2- dihydroquinoline (I) with 1-chloro-2, 3-epoxypropane (II). Instead of expected O-alkylation, which is typical of reactions of II with phenols [1], oxidation of quinoline I occurred to give 2, 2, 4-trimethyl-2, 6-dihydroquinolin-6-one (III):
