4-Chloro-2,3,5-trimethyl-1-oxidopyridin-1-ium → 4-Methoxy-2,3,5-trimethylpyridine 1-oxide

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Reaction Steps

0.86 g (5 mmol) 4-chloro-2,3,5-trimethylpyridine N-oxide and 8.5 ml 2M sodium methoxide was heated in a closed vessel to 70° C. for 16 hrs. Gave after work up 92% yield of 4-methoxy-2,3,5-trimethylpyridine N-oxide. Addition of 20% dimethylsulfoxide to the solvent increases the reaction rate but complicates the work up. The product was obtained as a waxy solid. NMR: 2×3H, 2,25; 3H, 2,5(s); 3H, 3,80(s); 1H, 8,2(s). (CDCl3).

Provenance & Evidence