Sodium Hydroxide → 4-Methoxy-5-methoxycarbonyl-nicotinic acid

Participants

Reaction Steps

To a solution of 5.3 g (23.5 mmol) of methyl-4-methoxy-5-methoxycarbonyl-nicotinate in 150 ml of methanol and 50 ml of water is added a solution of 0.94 g (23.5 mmol) of sodium hydroxide in 10 ml of water. The resulting mixture is stirred at room temperature overnight. The methanol is removed under vacuum, the aqueous solution is made slightly acidic and extracted with ethyl acetate. The combined organic phases are dried and filtered through silica. The filtrate is evaporated to near dryness and diluted with diisopropyl ether. A precipitate is obtained, filtered off and dried. There is obtained 2.83 g (57% yield) of a white solid (M+1=212).

Provenance & Evidence