5-Acetyl-2-hydroxy-6-methylnicotinonitrile → 5-acetyl-6-methyl-2(1H)-pyridinone

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Reaction Steps

5-acetyl-1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile (2.32 g, 0.013 mole) and concentrated HCl (50 ml) were heated and stirred at reflux under an argon atmosphere for 5 hours. Upon cooling to room temperature a solid precipitated. The solid was collected by filtration and allowed to air dry. The dry solid (1.25 g) was heated to 280°-290° C. and maintained at this temperature for 7 minutes. The residue was allowed to cool to room temperature then extracted into methylene chloride. Concentration of the methylene chloride solution followed by flash chromatography (50% methylene chloride--ethyl acetate) gave 0.46 g m.pt. 201°-202° C. (1:t 196°-198° C.).

Provenance & Evidence