Novel Methylation(第6報) : サリチル酸メチルおよび蓚酸ジメチルによる1級アミンおよび2級アミンのN-メチル化反応 : 複素環式化合物の合成研究第223報

概要

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It was found that heating of methyl carboxylate with primary or secondary amine, in equimolar amounts, without the use of a solvent, sometimes afforded the corresponding amide as the chief product, and sometimes N-methylated secondary amine, tertiary amine, and quaternary ammonium compound. Based on these facts and considering the result of a reaction betewen methyl carboxylate and a tertiary amine, reaction of methyl carboxylate and an amine would proceed toward amidolysis or methylation. This is thought to be due to the attack of the lone-pair electrons of the nitrogen on the carbonyl-carbon, resulting in amidolysis, and when such an attack is interfered by the basicity of nitrogen and a steric effect (F-strain), resulting in attack on the methylcarbon to produce methylation.
公益社団法人日本薬学会の論文
1968-04-25