Hydrochloric Acid → 2-Hydroxy-5-phenylnicotinic acid

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Reaction Steps

A mixture of 25.49 g. of 3-amino-2-phenyl-2-propenal and 27.32 g. of dimethyl malonate is reacted with 18.36 g. of sodium methoxide in one liter of methanol. The solution is stirred for 2 hours at room temperature and then is heated at reflux temperature for 3 hours. The resulting mixture is cooled and filtered to collect the precipitate. The solid is suspended in water and acidified with 10% aqueous hydrochloric acid to give a white solid. The solid is collected and washed with water followed by ethanol to yield 18.0 g. of methyl 1,2-dihydro-2-oxo-5-phenyl-3-pyridinecarboxylate. The ester is hydrolyzed by heating at reflux temperature for 2.5 hours in the presence of concentrated hydrochloric acid to give the product of the Example, m.p. 296° C. dec.

Provenance & Evidence