Ammonium formate → HCID 22939450, compound

HRID 748406

Reaction equation

HRID 748406 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=[CH:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14].C([O-])=O.[NH4+]>C(O)C.O.[C].[Pd]>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14]

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 684573677-(2-Pyridyl)-6-heptenoic acid

Product 1

HCID 22939450HCID 22939450, compoundYield 91.4%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

7-(2-Pyridyl)-6-heptenoic acid (0.97 g, 4.7 mmol) was dissolved in ethanol (15 ml), and 10% palladium-carbon (0.16 g) and a solution of ammonium formate (1.7 g, 27.0 mmol) in water (2 ml) were added thereto. The reaction 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 magnesium sulfate. The solvent was concentrated under reduced pressure to give the titled compound (0.89 g, 91%).

Workup

  1. temperatureThe reaction 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 magnesium sulfate
  7. concentrationThe solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5428920960a849a3ae83f89e301623bc
Source dataset
uspto-grants-2008_07
Patent number
US07399759B2

Linked notes

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