Hydrochloric Acid → (2',3-Dimethyl-[2,4'-bipyridin]-5-yl)methanamine hydrochloride

Participants

Reaction Steps

To a 2-L Parr-Shaker Reactor was charged 2′,3-dimethyl-[2,4′-bipyridine]-5-carbaldehyde oxime (34f, 560 mmol), Pd/C (23 g, 112 mmol, 50 wt % wet), conc. HCl (94 mL), and ethanol (600 mL). The reaction mixture was shaked at rt under 40 psi H2 until H2 was consumed. After filtration through Celite, the filtrate was solvent-exchanged to ethanol by repeating the concentration and refilling with ethanol twice. The product was stirred in ethanol/iso-propyl acetate (800 mL, v 1/1) at rt for 18 h. The solid was collected by filtration and rinsed with EtOH/iso-propyl acetate (400 mL, v 1/1). The wet cake was dried at 50° C. under vacuum for 18 h to afford (2′,3-dimethyl-[2,4′-bipyridin]-5-yl)methanamine hydrochloride (34g) as a light yellow powder. 1H NMR (500 MHz, DMSO-d6) δ ppm 2.44 (s, 3H), 2.89 (s, 3H), 4.15 (q, J=5 Hz, 2H), 8.05 (dd, J=1.6, 6.0 Hz, 1H), 8.10 (d, J=1.6 Hz, 1H), 8.13 (s, 1H), 8.76 (d, J=2.0 Hz, 1H), 8.85 (d, J=6.0 Hz, 1H), 8.88 (brd, 3H).

Provenance & Evidence