Hydrochloric Acid → 3-Pyridinecarboxylic acid, hydrochloride

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Reaction Steps

A solution of 9.4 g of 2,2-dimethyl-5-(2,5-dimethylphenoxy)pentanol in 50 ml of methylene chloride is added dropwise to an ice-cold solution of 7.12 g of nicotinyl chloride hydrochloride in 150 ml of methylene chloride containing 8.08 g of triethylamine. The mixture is heated for two hours. Upon cooling, the mixture is washed with water, dried over anhydrous magnesium sulfate and evaporated to dryness to give the 2,2-dimethyl-5-(2,5-dimethylphenoxy)pentyl ester of 3-pyridine carboxylic acid as an oil. The crude 2,2-dimethyl-5-(2,5-dimethylphenoxy)pentyl ester of 3-pyridine carboxylic acid is converted to its hydrochloride salt by treatment with hydrogen chloride to yield the desired 2,2-dimethyl-5-(2,5-dimethylphenoxy)pentyl ester of 3-pyridine carboxylic acid, monohydrochloride, m.p. 129°-130° C. following crystallization from isopropanol; yield 5 g.

Provenance & Evidence