Ammonia → 3-(aminomethyl)-4-ethyl-6-methylpyridin-2(1H)-one

HRID 1616834Notes

Reaction equation

HRID 1616834 reaction equation
[CH2:1]([C:3]1[CH:8]=[C:7]([CH3:9])[NH:6][C:5](=[O:10])[C:4]=1[C:11]#[N:12])[CH3:2].N>[Ni].CO>[NH2:12][CH2:11][C:4]1[C:5](=[O:10])[NH:6][C:7]([CH3:9])=[CH:8][C:3]=1[CH2:1][CH3:2]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 156418004-Ethyl-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

Product 1

HCID 674665833-(aminomethyl)-4-ethyl-6-methylpyridin-2(1H)-oneYield 54.6%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a suspension of Raney Nickel (6 g) in methanol (200 mL) was added 4-ethyl-1,2-dihydro-6-methyl-2-oxopyridine-3-carbonitrile (10 g, 61.7 mmol) and methanolic ammonia (750 mL). The reaction mixture was stirred at room temperature under hydrogen pressure (80 psi) for 48 hrs. The reaction mixture was filtered through Celite and washed with methanol (250 mL). The filtrate was concentrated under reduced pressure and the residue purified by filter column using silica gel (60-120 mesh), eluted with 10% MeOH in CHCl3, to afford 3-(amino methyl)-4-ethyl-6-methylpyridin-2(1H)-one (5.6 g, 54%) as an off white solid. 1H NMR (DMSO-D6, 400 MHz) (free amine): 6 ppm 1.063-1.101 (t, 3H, J=7.6 Hz), 2.101 (s, 3H), 2.412-2.449 (m, 2H), 3.448 (s, 2H), 5.835 (s, 1H). MS (ES) [M+H]+ 167.06.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. washwashed with methanol (250 mL)
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue purified
  5. filtrationby filter column
  6. washeluted with 10% MeOH in CHCl3

Sources & evidence

ORD record
ord-3646a4fb57fb48a8b3fea69d8f600447
Source dataset
uspto-grants-2014_07
Patent number
US08765792B2

Reaction notes

Loading…