The general procedure for the synthesis of 2-aminomethyl-5-chloropyridine from 5-chloro-2-cyanopyridine was as follows: 5-chloropyridinecarbonitrile (3.8 g, 27.43 mmol) was dissolved in ethanol (100 mL), and concentrated HCl (3 mL) and 10% Pd-C catalyst (1.0 g) were added. The reaction mixture was shaken under hydrogen atmosphere (40 psi) for 2 hours. After completion of the reaction, the catalyst was removed by filtration and the filtrate was concentrated. The obtained residue was dissolved in saturated NaHCO3 solution (50 mL) and extracted with dichloromethane (4 x 25 mL). The organic phases were combined, dried with anhydrous Na2SO4, filtered and concentrated to afford 2-aminomethyl-5-chloropyridine as a yellow oil (2.0 g, 51% yield). The product was analyzed by LCMS showing a (M + H)+ peak of 143.07 (calculated value: 143.04, C6H8ClN2).1HNMR (500 MHz, CDCl3) δ ppm: 8.56-8.51 (1H, br d), 7.66-7.60 (1H, m), 7.28-7.14 (1H, m), 3.97 (2H. s), 1.72 (2H, s).
