Hydrochloric Acid → 6-Methoxy-3-nitropyridine-2-acetonitrile

Participants

Reaction Conditions

Reaction Steps

Under argon and in an anhydrous medium, 15 g (97.3 mmol) of 2-methoxy-5-nitropyridine and 17.9 g (107 mmol) of 4-chlorophenoxyacetonitrile are dissolved in 300 ml of anhydrous tetrahydrofuran; the solution is added by transfer to a solution of 24 g (214 mmol) of potassium tert-butylate in 220 ml of anhydrous tetrahydrofuran maintained at a temperature below −10° C. The reaction mixture is stirred for three hours at a temperature of from −10 to −15° C. An aqueous 5% hydrochloric acid solution (170 ml) is added dropwise to the reaction mixture, maintaining the temperature at −10° C. The mixture is extracted with ethyl acetate. After drying over magnesium sulphate and evaporation, the residue is purified by flash chromatography over silica gel (eluant: petroleum ether/ethyl acetate, 2:1). After washing with a petroleum ether/diethyl ether mixture (2:1), the title compound is obtained in the form of a brown product.

Provenance & Evidence