Amide ion formation and N-alkylation of aminoanthraquinones in the presence of potassium hydroxide in dimethyl sulfoxide.

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概要

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• Amide ions were formed by the deprotonation of the amino group of amino- and (monoalkylamino)anthraquinones in the presence of powdered potassium hydroxide in dimethyl sulfoxide (DMSO). Under a nitrogen atmosphere these amide ions changed to their radical anions. The amide ions of 1-aminoanthraquinones reacted with excess alkyl halides to yield 1-alkylaminoanthraquinones, while the <I>N</I>-alkylation of 2-aminoanthraquinones afforded 2-dialkylaminoanthraquinones in good yields. 2-Aminobenzophenone underwent mono-<I>N</I>-alkylation, while 4-aminoazobenzene and p-nitroaniline underwent di-<I>N</I>-alkylation. It was also found that the carbanion of DMSO easily attacked the carbonyl group of the (dialkylamino)anthraquinones.

• 公益社団法人 日本化学会の論文

著者

• Arai Sadao

  Department Of Chemistry Tokyo Medical University

• Hida Mitsuhiko

  Department of Industrial Chemistry, Faculty of Technology, Tokyo Metropolitan University

• Kato Seijiro

  Department of Industrial Chemistry, Faculty of Technology, Tokyo Metropolitan University

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