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Communication | Special issue | Vol 11, No. 1, 1978, pp.371-376
Published online, 1st January, 1970
DOI: 10.3987/S(N)-1978-01-0371
A Preliminary Study on Phase-tranfer Catalyzed Reaction of Aromatic N-Oxide Derivatives. Reaction of 4-Chloroquinoline 1-Oxide with Carbanions

Masatomo Hamana,* Fuminori Sato, Yoshio Kimura, Makoto Nishikawa, and Hiroshi Noda

*Faculty of Pharmaceutical Sciences, Kyushu University, 3-1-1 Maidashi, Higashi-ku, Fukuoka 812-8582, Japan

Abstract

A solution of 4-chloroquinoline 1-oxide (1) and α-phenylpropionitrile in benzene was treated with 50% sodium hydroxide and a catalytic amount of tetrabutyl-ammonium bromide at 50° for 8 hr with vigorous stirring to produce 4-(α-cyano-α-phenyl)ethylquinoline 1-oxide in 72% yield. Reactions of 1 with butyl vinyl ether adducts of some aromatic aldehyde cyanohydrins under the same conditions gave, after hydrolysis with hot 10% hydrochloric acid, 4-aroylquinoline 1-oxides.