Ammonium formate → 4-Pyridinepropanenitrile

HRID 499609Notes

Reaction equation

HRID 499609 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]=[CH:8][C:9]#[N:10])=[CH:3][CH:2]=1.C([O-])=O.[NH4+]>C(O)C.O.[C].[Pd]>[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][C:9]#[N:10])=[CH:3][CH:2]=1

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 534078083-Pyridin-4-YL-acrylonitrile

Product 1

HCID 73304614-PyridinepropanenitrileYield 67%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

3-(4-Pyridyl)acrylonitrile (1.3 g, 10.0 mmol) was dissolved in ethanol (10 ml), and 10% palladium-carbon (0.13 g) and a solution of ammonium formate (2.5 g, 40.0 mmol) in water (3 ml) were added thereto. The reaction mixture was refluxed for 2.5 hrs. Palladium-carbon was filtered off, and the reaction mixture was combined with ethyl acetate and water. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The reaction mixture was subjected to a silica gel (25 g) column chromatography. The fractions eluted with hexane-ethyl acetate (1:1, v/v) were collected and concentrated to give the titled compound (0.88 g, 67%).

Workup

  1. temperatureThe reaction mixture was refluxed for 2.5 hrs
  2. filtrationPalladium-carbon was filtered off
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. washThe fractions eluted with hexane-ethyl acetate (1:1
  6. customv/v) were collected
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4c551311597947b2907e1000765ed115
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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