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

Temperature

-12.5 °C

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.

1. temperaturemaintained at a temperature below −10° C
2. temperaturemaintaining the temperature at −10° C
3. extractionThe mixture is extracted with ethyl acetate
4. dry with materialAfter drying over magnesium sulphate and evaporation
5. customthe residue is purified by flash chromatography over silica gel (eluant: petroleum ether/ethyl acetate, 2:1)
6. washAfter washing with a petroleum ether/diethyl ether mixture (2:1)

ORD record

ord-782c097be4ad4547a3105698118c2ca6

Source dataset

uspto-grants-2002_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06495543B1