Formic Acid → HCID 178471160, compound

HRID 349922Notes

Reaction equation

HRID 349922 reaction equation
C([N:8]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:11](/[CH:19]=[CH:20]/[C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:10]=[N:9]1)C1C=CC=CC=1.C(O)=O>[C].[Pd].C(O)C>[C:13]1([C:12]2[C:11]([CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:10][NH:9][N:8]=2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 2

HCID 284Formic AcidHCID 69421709ethyl(E)-3-(1-benzyl-5-phenyl-1H-pyrazol-4-yl)propenoate

Product 1

HCID 178471160HCID 178471160, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A mixture of ethyl(E)-3-(1-benzyl-5-phenyl-1H-pyrazol-4-yl)propenoate (300 mg), 5% palladium-carbon (600 mg), formic acid (3 ml), and ethanol (10 ml) was refluxed for 2 hours. After the palladium-carbon was removed by filtration, the filtrate was concentrated. The residue was dissolved in ethyl acetate, washed with saturated aqueous sodium bicarbonate and then with saturated aqueous sodium chloride solution, dried (MgSO4), and concentrated. The residue was subjected to silica gel column chromatography, and ethyl 3-(3-phenyl-1H-pyrazol-4-yl)propionate (120 mg, yield: 55%) was obtained as a colorless oily substance from the fraction eluted with ethyl acetate-hexane (2:3, volume ratio).

Workup

  1. temperaturewas refluxed for 2 hours
  2. customAfter the palladium-carbon was removed by filtration
  3. concentrationthe filtrate was concentrated
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with saturated aqueous sodium bicarbonate
  6. dry with materialwith saturated aqueous sodium chloride solution, dried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-683a847c3939419b9d3560a82b15c42f
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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