Reductive desulfurization of 3-cyano-2-methylthiopyridines under the action of Raney nickel |
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Authors: | A A Zubarev V K Zav’yalova V P Litvinov |
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Institution: | (1) N. D. Zelinsky Institute of Organic Chemistry, Russian Akademy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation |
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Abstract: | The action of Raney nickel on substituted 3-cyano-2-methylthiopyridines was studied. Under conditions of catalytic hydrogenation,
the reaction yields a mixture containing the aminosulfide resulting from reduction of the nitrile group with retention of
the methylthio group, the nitrile resulting from elimination of the methylthio group, and the amine resulting from both reduction
of the nitrile group and elimination of the methylthio group. Treatment of 3-cyano-2-methylthiopyridines with a large amount
of Raney nickel under desulfurization conditions induces simultaneous elimination of the methylthio group and reduction of
the nitrile group to the aminomethyl group. When reductive desulfurization is carried out in methanol or THF, primary amines
are formed, while the reactions in isopropyl or ethyl alcohol give secondary or tertiary amines, which are formed upon alkylation
of the amino group with alcohols.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2497–2500, November, 2005. |
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Keywords: | 3-cyano-2-methylthiopyridines 3-aminomethylpyridines primary secondary and tertiary amines Raney nickel reduction desulfurization salts of amines |
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