4-Ethyl-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile → 3-(aminomethyl)-4-ethyl-6-methylpyridin-2(1H)-one

HRID 2208935Notes

Reaction equation

HRID 2208935 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]>CO.N.[Ni]>[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 1

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

Product 1

HCID 674665833-(aminomethyl)-4-ethyl-6-methylpyridin-2(1H)-one

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

To a solution of 4-ethyl-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (1 eq) in methanol and aq. ammonia solution (9:1) was added a catalytic amount of Raney Nickel. The reaction mixture was stirred at room temperature under hydrogen pressure (balloon pressure) for 2-5 h. On completion of reaction, it was filtered through a celite bed and the filtrate was concentrated under reduced pressure to afford the title compound.

Workup

  1. customOn completion of reaction, it
  2. filtrationwas filtered through a celite bed
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c047b1cfbc2e4aea8b0f165888e2fa4e
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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