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Paper | Regular issue | Vol 65, No. 9, 2005, pp.2095-2105
Published online, 22nd July, 2005
DOI: 10.3987/COM-05-10462
Facile Synthesis of 3-Substituted and 1,3-Disubstituted Quinolin-2(1H)-ones from 2-Nitrobenzaldehydes

Kwanghee Koh Park* and Jin Young Jung

*Department of Chemistry, Chungnam National University, Yusung, Daejon 305-764, Korea

Abstract

2-Nitrobenzaldehydes were reduced with iron powder to 2-aminobenzaldehydes, which were reacted immediately with acyl chlorides to provide 2-carboxamidobenzaldehydes (1) with overall yields of 71-90 %. Reaction of 1 with base provided 3-substituted quinolin-2(1H)-ones with 63-97 % yields. Treatment of 1 with methyl iodide and base gave 1-methyl-3-substituted quinolin-2(1H)-ones with 82-95 % yields, whereas the treatment with isopropyl iodide gave 1-isopropyl-3-substituted quinolin-2(1H)-ones with 7-42 % yields.