Ammonia → 3-(aminomethyl)-4-(methoxymethyl)-6-methyl-2(1H)-Pyridinone

HRID 1854064Notes

Reaction equation

HRID 1854064 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[C:8]([CH3:10])[NH:7][C:6](=[O:11])[C:5]=1[C:12]#[N:13].N>CO.[Ni]>[NH2:13][CH2:12][C:5]1[C:6](=[O:11])[NH:7][C:8]([CH3:10])=[CH:9][C:4]=1[CH2:3][O:2][CH3:1]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 949992-Methyl-4-methoxymethyl-5-cyano-6-oxypyridine

Product 1

HCID 552557633-(aminomethyl)-4-(methoxymethyl)-6-methyl-2(1H)-PyridinoneYield 80%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-(methoxymethyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (0.165 g, 0.927 mmol) in methanol (10 mL), Raney Ni and ammonia (1 mL) were added and reaction stirred under hydrogen balloon pressure for 3 h. On completion, reaction mass was filtered through celite bed and filtrate concentrated to obtain the desired compound (0.13 g, 80%).

Workup

  1. customreaction
  2. customOn completion, reaction mass
  3. filtrationwas filtered through celite bed and filtrate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-492d465bba91488f8c95267828c0c0a1
Source dataset
uspto-grants-2015_02
Patent number
US08962620B2

Reaction notes

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