Hydrochloric Acid → 2-(2-Oxo-2,3-dihydroimidazo[1,2-a]pyridin-3-yl)butanedioic acid

Participants

Reaction Conditions

Reaction Steps

A hot solution of 80 g (2 moles) of sodium hydroxide in 200 ml of water is added in portions, while stirring, to a mixture of 341 g (2 moles) of the hydrochloride of imidazo[1,2-a]pyridin-2(3H)-one in 700 ml of water. Then, a solution of 250.7 g (2.16 moles) of maleic acid in 600 ml of water is added dropwise in such a manner that the internal temperature of the reaction mixture remains between 40° and 45° C. After 30 hours at room temperature (20°-25° C.) the mixture is cooled to 5° C., the resulting precipitate is filtered off, the filtrate is concentrated in vacuo to approximately half its volume, and the resulting product is filtered with suction. The combined residues are washed with a little cold methanol and dried in vacuo at 50° C. 400 g of 3-(1,2-dicarboxyethyl)-imidazo[1,2-a]pyridin-2(3H)-one having a melting point of 193° (decomposition) are obtained. The resulting product is stirred at room temperature for 6 hours with 650 ml of concentrated hydrochlorid acid. After cooling to 5° C., the precipitate is filtered off, the filtrate is concentrated in vacuo to approximately half its volume and the resulting product is filtered with suction. The combined residues are washed with acetone and dried in vacuo at 50° C. In this manner the hydrochloride of 3-(1,2-dicarboxyethyl)-imidazo[1,2-a]pyridin-2(3H)-one having a melting point of 205° C. (decomposition) is obtained.

Provenance & Evidence