The Synthesis of 1-Methyl-2-pyridones from 2-Chloromethylpyridines
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概要
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The reaction of 2-chloromethylpyridine (Ia) and its homologs, 5-ethyl- (Ib), 6-methyl- (Ic), and 4-methyl-2-chloromethylpyridine (Id), with pyridine gave the corresponding 1-(2′-pyridylmethyl)-pyridinium chlorides (II), from which, on heating with dimethyl sulfate, 1-methyl-2-(pyridiniomethyl)-pyridinium salts (III) were obtained. The pyridinium salts were treated with aqueous alkali at a low temperature to yield 1-methyl- (IVa), 5-ethyl-1-methyl- (IVb), 1,6-dimethyl- (IVc), and 1,4-dimethyl-2-pyridone (IVd). The reaction sequence, in combination with the 1-oxidation of 2-picolines and followed by the reaction of the 1-oxides with tosyl chloride to yield 2-chloromethylpyridines, is recommended as a convenient route for the synthesis of 1-methyl-2-pyridones starting with 2-picolines.
- 公益社団法人 日本化学会の論文
著者
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Ishibashi Fumihide
Department of Chemistry
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Matsumura Eizo
Department of Chemistry
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Nashima Takeo
Department Of Chemistry
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