6-Methyl-2-oxo-4-propyl-1,2-dihydropyridine-3-carbonitrile → 3-(Aminomethyl)-6-methyl-4-propylpyridin-2(1H)-oneacetate

HRID 1959307Notes

Reaction equation

HRID 1959307 reaction equation
[CH3:1][C:2]1[NH:7][C:6](=[O:8])[C:5]([C:9]#[N:10])=[C:4]([CH2:11][CH2:12][CH3:13])[CH:3]=1>CO.N.[Ni]>[NH2:10][CH2:9][C:5]1[C:6](=[O:8])[NH:7][C:2]([CH3:1])=[CH:3][C:4]=1[CH2:11][CH2:12][CH3:13]

Participants

5

Reactant 1

HCID 156418016-Methyl-2-oxo-4-propyl-1,2-dihydropyridine-3-carbonitrile

Product 1

HCID 671241403-(Aminomethyl)-6-methyl-4-propylpyridin-2(1H)-oneacetateYield 92%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

To a solution of 6-methyl-2-oxo-4-propyl-1,2-dihydropyridine-3-carbonitrile (1.3 g, 7.38 mmol) in methanol and aq. ammonia solution (50 mL, 9:1), catalytic amount of Raney Nickel was added. Reaction mass was stirred at room temperature under hydrogen pressure (balloon pressure) for 5 h. On completion of reaction, it was filtered through celite bed and filtrate was concentrated under reduce pressure to afford the title compound (1.2 g, 92%).

Workup

  1. customReaction mass
  2. customOn completion of reaction, it
  3. filtrationwas filtered through celite bed and filtrate
  4. concentrationwas concentrated

Sources & evidence

ORD record
ord-4ebdebac05ea494893180d0d78190b50
Source dataset
uspto-grants-2013_04
Patent number
US08410088B2

Reaction notes

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