Ammonia → 3-(aminomethyl)-2,6-dimethylpyridin-4(1H)-one hydrochloride

A 250 mL Erlenmeyer flask was charged with 2,6-dimethyl-4-oxo-1,4-dihydropyridine-3-carbonitrile (360 mg, 2.430 mmol) and cold 2 M ammonia in EtOH (39.5 mL, 79 mmol). Ethanol (40 mL) was added to solubilize the remaining reactant. The solution was passed through a Raney Ni cartridge on a continuous flow hydrogenation reactor (40 psi, 40° C., 1 mL/min) for 16 h. The reaction solvent was removed in vacuo and the residue was dissolved in EtOH (1 mL) and CHCl3 (15 mL), then concentrated in vacuo. The residue was dissolved and concentrated in CHCl3 (2×15 mL) and DCM (15 mL). The sticky residue was suspended in diethyl ether (30 mL) and treated with 4 M HCl in 1,4-dioxanes (10.63 mL, 42.5 mmol). The suspension was stirred at room temperature overnight, at which time the white solid was collected via vacuum filtration, washed with diethyl ether (10 mL), and dried under high vacuum to give 3-(aminomethyl)-2,6-dimethylpyridin-4(1H)-one hydrochloride (200 mg, 0.975 mmol, 80% yield) as a white solid. 1H NMR (400 MHz, CDCl3) δ 6.26 (br. s., 1H), 3.90 (br. s., 2H), 2.64 (s, 1H), 2.38 (s, 3H), 2.32 (s, 3H), 1.22-1.30 (m, 2H). MS(ES) [M+H]+ 152.9.

1. customThe reaction solvent was removed in vacuo
2. dissolutionthe residue was dissolved in EtOH (1 mL)
3. concentrationCHCl3 (15 mL), then concentrated in vacuo
4. dissolutionThe residue was dissolved
5. concentrationconcentrated in CHCl3 (2×15 mL)
6. filtrationwas collected via vacuum filtration
7. washwashed with diethyl ether (10 mL)
8. customdried under high vacuum

ORD record

ord-634c74c344dc43d79e90b86e9e701239

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09382234B2