Ammonium formate → HCID 22939391, compound

HRID 499605Notes

Reaction equation

HRID 499605 reaction equation
[CH3:1][C:2](=[CH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].C([O-])=O.[NH4+]>C(O)C.O.[C].[Pd]>[CH3:1][CH:2]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 68458630HCID 68458630, compound

Product 1

HCID 22939391HCID 22939391, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Ethyl 2-methyl-3-(2-pyridyl)acrylate (7.8 g, 41.0 mmol) was dissolved in ethanol (80 ml), and 10% palladium-carbon (1.0 g) and a solution of ammonium formate (11.2 g, 178 mmol) in water (20 ml) was added thereto. The mixture was refluxed for 2 hrs. Palladium-carbon was filtered off. The reaction mixture was combined with water, concentrated under reduced pressure to the half amount and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated to give the titled compound (7.2 g, 91%).

Workup

  1. temperatureThe mixture was refluxed for 2 hrs
  2. filtrationPalladium-carbon was filtered off
  3. concentrationconcentrated under reduced pressure to the half amount
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated

Sources & evidence

ORD record
ord-e9137a539c2d44c89a03a8986980428b
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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