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Communication | Special issue | Vol 17, No. 1, 1982, pp.177-181
Published online, 1st January, 1970
DOI: 10.3987/S-1982-01-0177
Nucleophilic Substitution of 4-Chloroguinoline 1-Oxide and Related Compounds by Means of Hydride Elimination

Masatomo Hamana,* Genji Iwasaki, and Seitaro Saeki

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

Abstract

The reaction of 4-chloroquinoline 1-oxide (1) with pinacolone and t-BuOK in t-BuNH2 at -10~-15°C gives 4-chloro-2-pinacolylquinoline 1-oxide in good yield by means of hydride-elimination. Similar reactions of 1 with acetone, 2-butanone, acetophenone, and ethyl and t-butyl acetates occur when treated with t-BuOK or n-BuLi in t-BuNH2 at -10~-15°C, or t-BuOK, KNH2 or NaNH2 in liq NH3 at -70°C. Reactions of this type proceed also with quinoline 1-oxide (2), 3-bromoquinoline 1-oxide (3), p-chloronitrobenzene (4) and nitrobenzene.