144605-36-7Relevant articles and documents
REINVESTIGATION OF NITROSATION OF METHYLPYRIDINES AND THEIR 1-OXIDES AND DEOXYGENATION OF 3-PYRIDINECARBALDEHYDE 1-OXIDE OXIME
Tagawa, Yoshinobu,Hama, Kazuya,Goto, Yoshinobu
, p. 1605 - 1612 (2007/10/02)
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 deg C led to 3-(3-methyl-4-pyridyl)methylpyridine.Deoxygenation of 3-pyridinecarbaldehyde 1-oxide oxime was effected in 78percent yieldby the action of t-butyldimethylsilyl chloride-imidazolesodium iodide-zinc followed by desilylation with tetrabutylammonium fluoride to give 3-pyridinecarbaldehyde oxime.