Acetaldehyde → HCID 11819193, compound

Participants

Reaction Steps

To a solution of 5-amino-3-cyanopyridine (300 mg, 2.52 mmol) in methanol (10 ml) was added acetaldehyde (1.42 ml, 25.1 mmol), and the mixture was stirred at room temperature for 10 minutes. Next, sodium cyanoborohydride (950 mg, 15.1 mmol) was added, and acetic acid was further added to adjust the pH of thereaction mixture to about 6. The mixture was stirred for 5 hours. After the reaction was completed, the reaction mixture was neutralized with an aqueous sodium carbonate solution and extracted with diethyl ether (30 ml×3). The diethyl ether layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (Wako Gel C-200, 20 g; eluted with chloroform:methanol=200:1) to give 3-cyano-5-ethylaminopyridine (200 mg, 1.36 mmol, yield 54%).

Provenance & Evidence