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Unusual Reaction of 2-Chloro-6,7-dialkoxyquinoline-3-aldoxime with Epichlorohydrin
Bhat, Neelima Balkrishen,Bhaduri, A.P.
, p. 431 - 434 (2007/10/02)
Unlike the reactions of 2-chloro- and 2-chloro-6-methoxyquinoline-3-aldoximes, the reaction of 2-chloro-6,7-dimethoxyquinoline-3-aldoxime (7) with epichlorohydrin gives 2-chloro-3-cyano-6,7-dimethoxyquinoline (13), 2-chloro-6,7-dimethoxyquinoline-3-aldoxime monomethyl ether (12), 6,7-dimethoxyisoxazoloquinoline (15), 2-chloro-6,7-dimethoxyquinoline-3-aldoxime-(2,3-epoxy)propyl ether (14), and 2-chloro-6,7-dimethoxyquinoline-3-aldoxime-(3'-methoxy-2'-hydroxy)propyl ether (16).However, 2-chloro-6,7-diethoxyquinoline-3-aldoxime (8) with epichlorohydrin affords the desired epoxy derivative (11) and a small quantity of 2-chloro-3-cyano-6,7-diethoxyquinoline (20).No definite reaction pathway could be delineated for the unusual reaction products of the reaction of 7 with epichlorohydrin.
