4-Cyano-pyridine-2-methanol

100-48-1

67-56-1

51454-63-8

Sulfuric acid (1.5 mL) was slowly added to a methanol (225 mL) solution of 4-cyanopyridine (15.7 g, 151 mmol) at room temperature, followed by heating and refluxing the mixture for 30 minutes. A solution of ammonium persulfate (54.9 g, 241 mmol) in water (100 mL) was added dropwise over 30 minutes under continuous reflux. After addition, the reaction was continued with stirring and reflux for 1 hour. Upon completion of the reaction, the solution was cooled to room temperature and the precipitate was collected by filtration. The filtrate was concentrated under reduced pressure to remove methanol. The pH was adjusted to 9 by adding saturated aqueous potassium carbonate to the residue and the precipitate was collected by filtration again. The filtrate was extracted with chloroform (100 mL × 4), the organic phases were combined and dried over anhydrous sodium sulfate. After the solvent was removed by evaporation under reduced pressure, the crude product was further purified by silica gel column chromatography (eluent: chloroform/methanol), and 2-(hydroxymethyl)isonicotinonitrile (7.95 g, yield 39%, off-white solid) was finally obtained.