Methanol → HCID 12795087, compound

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Reaction Steps

A solution of 8.6 g. of dimethyl 5,6,7,8-tetrahydropyrrolo[1,2-a]pyridine-1,8-dicarboxylate in 100 ml. of methanol is treated with a solution of 9.0 g. of potassium hydroxide in 100 ml. of water, and the reaction mixture is refluxed for 24 hours. The cooled solution is evaporated to dryness at a temperature of 30° C. and the residue is dissolved in the minimum amount of saturated sodium chloride solution. The resultant solution is acidified with concentrated hydrochloric acid and the precipitated solid is collected by filtration, washed with water and dried in vacuo. The mother liquor is extracted with ethyl acetate 3 times and the combined extracts are dried over magnesium sulfate and evaporated to dryness under reduced pressure and recrystallization of the combined residues from methanol yields 5,6,7,8-tetrahydropyrrolo[1,2-a]pyridine-1,8-dicarboxylic acid (VIII, R=H, n=1), m.p. 236°-237° C.

Provenance & Evidence