反应详情

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).

1. customwas shaked at rt under 40 psi H2 until H2
2. customwas consumed
3. filtrationAfter filtration through Celite
4. concentrationthe concentration
5. filtrationThe solid was collected by filtration
6. washrinsed with EtOH/iso-propyl acetate (400 mL, v 1/1)
7. customThe wet cake was dried at 50° C. under vacuum for 18 h