Hydrochloric Acid → 6-Methoxy-3-pyridineacetic acid

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Reaction Steps

2-(6-Methoxy-pyridin-3-yl)-malonic acid diethyl ester (5.6 g, 21.0 mmoL) prepared in Example 3 was dissolved in 2N NaOH/THF:H2O (1:1) (20 mL). The resulting mixture was heated to reflux for 3 hours. The reaction mixture was then adjusted to pH=1 by concentrated HCl and stirred at room temperature for another 1 hour. The solution was then adjusted to pH=13 by 1N NaOH and extracted with ether. The aqueous phase was acidified to pH=5 by 1N HCl and extracted 3× by ethyl acetate. The combined organic phase was then washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to give the title compound a white solid (2.45, 70%).

Provenance & Evidence