500732-62-7

205744-14-5

Triphenylphosphine (2.5 g, 9.5 mmol) was added to a solution of 3-azidomethyl-2-chloropyridine (1.4 g, 8.5 mmol) in anhydrous THF (30 mL) at 0 °C. The reaction mixture was slowly warmed to room temperature and stirred for 18 hours. Subsequently, NH4OH (3 mL) was added to the reaction mixture and stirring was continued for 3 hours. Next, the mixture was treated with 3M NaOH solution and stirred for 1 hour. The mixture was acidified to pH 2 by dropwise addition of 4 M HCl solution. after diluting the mixture with ether, the organic and aqueous layers were separated. The aqueous layer was extracted with ether and subsequently alkalized with 2M NaOH solution. The alkalized aqueous solution was extracted with CH2Cl2 (3×). The organic phases were combined, dried with MgSO4 and concentrated under reduced pressure to give a light yellow oily solid. The solid was diluted with ether and filtered. The filtrate was concentrated to give a light yellow oily substance. The crude product was purified by silica gel column chromatography using 20:1 CH2Cl2:MeOH as eluent to give 0.88 g (73% yield) of 3-aminomethyl-2-chloropyridine as a colorless oil.