Hydrochloric Acid → 3-oxo-3-(1H-pyrrol-2-yl)propanenitrile

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Reaction Steps

Into an ice-chilled solution of 30 g of pyrrole and 30 g of malononitrile in 800 ml of dry ether is passed by HCl for 20 minutes. After standing several hours the suspension is filtered to give 65 g of orange-brown, water-soluble solid. The solution of 50 g of this intermediate (the enamine nitrile hydrochloride) in 600 ml of water is covered with 400 ml of ethyl acetate and stirred for 21/2 hours at room temperature. The organic layer is separated, dried (MgSO4) and evaporated to give crystals, m.p. 77°-9°; additional product is obtained by warming the aqueous layer on steam cone for 1/2 hour and extracting with ethyl acetate. Recrystallization from water gives 2-pyrroloylacetonitrile, m.p. 79°-81°.

Provenance & Evidence