Formic Acid → HCID 178470746, compound

HRID 350019Notes

Reaction equation

HRID 350019 reaction equation
C([N:8]1[CH:12]=[C:11]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:10]([O:19][CH2:20][CH3:21])=[N:9]1)C1C=CC=CC=1.C(O)=O>[C].[Pd].C(O)C>[CH2:20]([O:19][C:10]1[C:11]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:12][NH:8][N:9]=1)[CH3:21]

Participants

5

Reactant 2

HCID 284Formic AcidHCID 69422643ethyl 1-benzyl-3-ethoxy-1H-pyrazol-4-ylacetate

Product 1

HCID 178470746HCID 178470746, compoundYield 54.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A mixture of ethyl 1-benzyl-3-ethoxy-1H-pyrazol-4-ylacetate (7.50 g), 5% palladium-carbon (15.0 g), formic acid (50 ml) and ethanol (100 ml) was refluxed for 1 hour. After cooling, the palladium-carbon was removed by filtration, and the filtrate was concentrated. The residue was dissolved in ethyl acetate, which was washed with saturated aqueous sodium bicarbonate solution, and with a saturated aqueous sodium chloride solution, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography to obtain ethyl 3-ethoxy-1H-pyrazol-4-ylacetate (2.79 g, yield 54%) as a colorless oily substance from the fraction eluted with ethyl acetate-hexane (1:1, volume ratio).

Workup

  1. temperaturewas refluxed for 1 hour
  2. temperatureAfter cooling
  3. customthe palladium-carbon was removed by filtration
  4. concentrationthe filtrate was concentrated
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwhich was washed with saturated aqueous sodium bicarbonate solution
  7. dry with materialwith a saturated aqueous sodium chloride solution, dried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-7a0de8350c5b4aba86cb2e78136613e6
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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