Hydrochloric Acid → HCID 23508474, compound

Participants

Reaction Steps

10 ml of dimethyl sulfoxide was added to the above potassium tert-butoxide, followed by cooling in an ice-water bath. While this mixture was kept at 20° C. or below, 1.882 g of 4-aminopyridine was added thereto, followed by stirring at room temperature for 1 hour. 1.21 g of 4-fluorobenzonitrile was dissolved in 3 ml of dimethyl sulfoxide, and this solution was added dropwise to the above reaction mixture kept at an internal temperature of 30° C. or below, followed by stirring at room temperature for 30 minutes. After water was added to the reaction mixture, the resulting mixture was acidified with dilute hydrochloric acid and then neutralized with a saturated aqueous solution of sodium hydrogen carbonate. The product was extracted with tetrahydrofuran-diethyl ether (1:1), and the organic layer was washed with water and dried over anhydrous sodium sulfate. After the solvent was distilled off, the resulting crude product was purified by silica gel column chromatography (using a 9:1 mixture of chloroform and methanol as the eluent) to obtain 1.85 g of 4-[N-(4-pyridyl)amino]benzonitrile.

Provenance & Evidence