Xu Bao-cai
2004
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Fine chemicals
Abstract
2,3,5-Trimethylpyridine was oxidized to 2,3,5-trimethylpyridine N-oxide(Ⅰ) in 91% yield by treatment with hydrogen peroxide in hot acetic acid.Ⅰ was nitrated with fuming nitric acid in conc. sulfuric acid to give 2,3,5-trimethyl-4-nitropyridine N-oxide(Ⅱ) in 80.4% yield.Treatment of Ⅱ with sodium methoxide afforded 4-methoxy-2,3,5-trimethylpyridine N-oxide(Ⅲ) in 91% yield.Heating Ⅲ with acetic anhydride gave 2-acetoxymethyl-4-methoxy-3,5-dimethylpyridine(Ⅳ) in 66.6% yield.Then Ⅳ was hydrolyzed to 2-hydroxymethyl-4-methoxy-3,5-dimethylpyridine(Ⅴ) in 93% yield.Finally,Ⅴ was halogenated with thionyl chloride to give 2-chloromethyl-4-methoxy-3,5-dimethylpyridine hydrochloride(Ⅵ) in 90.6% yield.Structure of Ⅵ was primarily identified by TLC,IR and ~1HNMR.