Hydrochloric Acid → 4-Ethoxy-2,3,5-trimethylpyridine 1-oxide

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Reaction Steps

4.2 g of sodium were dissolved in 780 ml of ethanol under argon. 22.3 g of 2,3,5-trimethyl-4-nitropyridine 1-oxide were then added portionwise thereto and the solution was left to boil under reflux overnight. The pH was adjusted to 7 by means of 5N hydrogen chloride in ethyl acetate while cooling and the mixture was then evaporated in vacuo. The residue was taken up in 0.5 l of methylene chloride, the solution was filtered through silica gel, which was rinsed with 200 ml of methylene chloride, the combined filtrates were evaporated in vacuo and the residue was crystallized from petroleum ether. There was obtained 4-ethoxy-2,3,5-trimethylpyridine 1-oxide of melting point 59°-61°.

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