Hydrochloric Acid → 5-Nitro-2-(2-cyanoethyl)-3-methylpyridine

Participants

Reaction Steps

3-(3-Methyl-5-nitropyrid-2-yl)-3,3-bis(carbethoxy)-propionitrile (29.8 g) was dissolved in methanol (1120 ml), molar sodium hydroxide solution (355 ml) was added, the reaction was cooled from 28° C. to room temperature and stirred for 55 minutes. The pH was lowered to 4 by the addition of concentrated hydrochloric acid, the reaction was stirred for 2.75 hr., the pH was then raised to 7 and the methanol was distilled off. The aqueous phase was extracted with chloroform, extracts were dried, filtered and concentrated. The residue was crystallised from chloroform/petroleum ether 40°-60° C. The crude product was treated with charcoal in ethanol and recrystallised from ethanol to give the title compound 10.44 g, m.p. 73°-74° C.

Provenance & Evidence