Acetic Acid → 3-Pyridinecarbonitrile, 1,2-dihydro-6-methyl-2-oxo-

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Reaction Steps

A mixture of 150 g (1.5 m) of 4-methoxy-3-buten-2-one, 126 g (1.5 m) of α-cyanoacetamide, and catalyst (6 cc of glacial acetic acid in 15 cc of water made basic with piperidine) in 750 cc of methyl cellosolve is refluxed and stirred for 3 hours. The solution which forms is concentrated in vacuo and the residue semi-solid is boiled in an excess of isopropanol and filtered hot. The first crop is dried to afford a 94.5 g (47%) yield of 3-cyano-6-methyl-2-pyridone, m.p. 245-246 dec. A mixture of 72 g (.537 m) of this product and 600 cc of 12N hydrochloric acid is refluxed and stirred for 6 hours. The solution is allowed to stand at room temperature for 3 days and is concentrated in vacuo. The residue solid is recrystallized with ethanol to afford a 43 g (52.5%) yield of 1H, 3-carboxy-6 -methylpyridin-2-one, m.p. 226°.

Provenance & Evidence