Hydrochloric Acid → 1H-Pyrrole-2-acetic acid, 1-methyl-, ethyl ester

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Reaction Steps

A 28 ml solution of ethereal hydrogen chloride (0.049 mole of HCl) is added dropwise over a 3 hr period to a solution of 2.1 g of N-methylpyrrole and 2.9 g of ethyl cyanoformate in 3 ml ether. The ether supernatant is decanted off, and the precipitate taken up in 11 mls of dry pyridine and the mixture transferred to a pressure bottle. Hydrogen sulfide (13 g) is added to the mixture at -78° C., the bottle sealed, and the mixture is stirred at ambient temperature overnight (about 16 hours). Gas chromatographic analysis with internal standards shows 57% yield of ethyl N-methylpyrrole-2-acetate.

Provenance & Evidence