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Paper | Regular issue | Vol 34, No. 8, 1992, pp.1605-1612
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6080
■ Reinvestigation of Nitrosation of Methylpyridines and Their 1-Oxides and Deoxygenation of 3-Pyridinecarbaldehyde 1-Oxide Oxime

Yoshinobu Tagawa, Kazuya Hama, and Yoshinobu Goto*

*Faculty of Pharmaceutical Sciences, Fukuoka University, Nanakuma, Jonan-ku, Fukuoka, 814-01, Japan

Abstract

Treatment of methylpyridines and their 1-oxides with t-butyl nitrite in the presence of potassium t-butoxide in liquid ammonia afforded the corresponding aldoximes in good yields except for the case of 3-methylpyridine. The reaction of 3-methylpyridine with t-butyl nitrite in the presence of lithium 2,2,6,6-tetramethylpiperidide and N,N,N’,N’-tetramethylethylenediamine in tetrahydrofuran at -78 °C led to 3-(3-methyl-4-pyridyl)methylpyridine. Deoxygenation of 3-pyridinecarbaldehyde 1-oxide oxime was effected in 78% yield by the action of t-butyldimethylsilyl chloride-imidzole-sodium iodide-zinc followed by desilylation with tetrabutylammonium fluoride to give 3-pyridinecarbaldehyde oxime.