4-Vinylnicotinonitrile → 4-Ethylpyridine-3-carbonitrile

HRID 1830861Notes

Reaction equation

HRID 1830861 reaction equation
[CH:1]([C:3]1[C:8]([C:9]#[N:10])=[CH:7][N:6]=[CH:5][CH:4]=1)=[CH2:2]>C(OCC)(=O)C.[C].[Pd]>[CH2:1]([C:3]1[C:8]([C:9]#[N:10])=[CH:7][N:6]=[CH:5][CH:4]=1)[CH3:2]

Participants

4

Reactant 1

HCID 220497874-Vinylnicotinonitrile

Product 1

HCID 217660084-Ethylpyridine-3-carbonitrileYield 84%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The compound (25) (0.73 g, 5.61 mmol) was dissolved in ethyl acetate (15 ml) and 10% palladium carbon (20 mg) was added. The mixture was stirred at normal temperature and normal pressure under a hydrogen atmosphere for 2 hrs. for hydrogenation. The reaction mixture was passed through celite and the filtrate was partitioned between ethyl acetate and brine. The aqueous layer was extracted with ethyl acetate, and the extract was combined and dried (MgSO4). The solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give a colorless oil (0.62 g, 84%).

Workup

  1. customthe filtrate was partitioned between ethyl acetate and brine
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. dry with materialdried (MgSO4)
  4. customThe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b925a0658e7f49edae20a39078f518b4
Source dataset
uspto-grants-2006_06
Patent number
US07067537B2

Reaction notes

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