Hydrochloric Acid → (5-Chloropyridin-2-yl)methanamine

Participants

Reaction Steps

A solution of 5-chloropicolinonitrile (3.8 g, 27.43 mmol), conc.HCl (3 mL) and 10% Pd—C (1.0 g) in ethanol (100 mL) was shaken under a hydrogen atmosphere (40 psi) for 2 h. The reaction mixture was filtered, concentrated and the resulting residue taken up in satd NaHCO3 (50 mL) and extracted with CH2Cl2 (4×25 mL). The combined CH2Cl2 layers were dried (Na2SO4), filtered and concentrated to give the title compound as a yellow oil (2.0 g, 51% yield). LCMS (M+H) calcd for C6H8ClN2: 143.04. found: 143.07. 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).

Provenance & Evidence