Formic Acid → 4-Oxo-4H-chromene-3-carbonitrile

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Reaction Steps

A mixture of 26.1 g. (0.15 mole) of 4-oxo-4H-1-benzopyran-3-carboxaldehyde, 13.1 g. (0.19 mole) of hydroxylamine hydrochloride, 18.4 g. (0.27 mole) of sodium formate and 250 ml of 99% formic acid was heated with stirring at reflux for 21/2 hours. Water was added to 1-liter volume. The separated solid was filtered from the cooled mixture, washed well with water and dried to give 13 g. (51%) of crude nitrile melting at 138°-145°C. Recrystallization from ethylacetate gave pure, white crystals melting at 174°-176°.

Provenance & Evidence