Ammonia → 3-(Aminomethyl)-6-methyl-4-propylpyridin-2(1H)-oneacetate

Participants

Reaction Steps

To a suspension of Raney Ni (2 g) in methanol (250 mL) was added 1,2-dihydro-6-methyl-2-oxo-4-propylpyridine-3-carbonitrile (5 g, 28.4 mmol) and methanolic ammonia (750 mL). The reaction mixture was stirred at room temperature under hydrogen pressure (60 psi) for 48 hrs. The reaction mixture was filtered through celite pad and washed with methanol (250 mL). The filtrate was concentrated under reduced pressure to afford the crude product (5.1 g). The crude product was purified by column chromatography by using a short column of silica gel (60-120 mesh) treated with methanolic NH3, (eluant: 0-25% methanol in DCM) and isolated to afford the desired product 3-(amino methyl)-6-methyl-4-propylpyridin-2(1H)-one as an off white solid (2 g, 39% yield). 1H NMR (DMSO, 400 MHz): δ 0.921 (t, 3H, J=7.2 Hz), 1.518 (m, 2H), 2.09 (s, 3H), 2.418 (t, 2H, J=7.6 Hz), 3.451 (s, 2H), 4-5.6 (br s, 2H, exchangeable), 5.822 (s, 1H). LCMS E-S (M+H)=181.22.

Provenance & Evidence