Citric Acid → 5-Methyl-1-[2'-(trifluoromethoxy)-1,1'-biphenyl-3-yl]-1H-pyrazole-3-carboxylic acid

HRID 733130Notes

Reaction equation

HRID 733130 reaction equation
C([O:3][C:4]([C:6]1[CH:10]=[C:9]([CH3:11])[N:8]([C:12]2[CH:13]=[C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[O:24][C:25]([F:28])([F:27])[F:26])[CH:15]=[CH:16][CH:17]=2)[N:7]=1)=[O:5])C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO.[OH-].[Na+].O>[CH3:11][C:9]1[N:8]([C:12]2[CH:13]=[C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[O:24][C:25]([F:28])([F:26])[F:27])[CH:15]=[CH:16][CH:17]=2)[N:7]=[C:6]([C:4]([OH:5])=[O:3])[CH:10]=1

Participants

6

Reactant 2

HCID 311Citric AcidHCID 11417896Ethyl-5-methyl-1-[2'-(trifluoromethoxy)-1,1'-biphenyl-3-yl]-1H-pyrazole-3-carboxylate

Product 1

HCID 112453825-Methyl-1-[2'-(trifluoromethoxy)-1,1'-biphenyl-3-yl]-1H-pyrazole-3-carboxylic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of ethyl-5-methyl-1-[2′-(trifluoromethoxy)-1,1′-biphenyl-3-yl]-1H-pyrazole-3-carboxylate (0.39 g, 1 mmol) (from EXAMPLE 3) in a mixture of MeOH (5 ml) and 2N NaOH (2 ml) was refluxed for 16 hours. The reaction was then cooled, diluted with water, acidified with 10% citric acid and extracted with ethylacetate. The organic phase was washed with water, dried (sodium sulfate) and concentrated in vacuo to give the titled product.

Workup

  1. temperaturewas refluxed for 16 hours
  2. temperatureThe reaction was then cooled
  3. extractionextracted with ethylacetate
  4. washThe organic phase was washed with water
  5. dry with materialdried (sodium sulfate)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c7e4ac8ac2f84f87b186de9e9e14f5b0
Source dataset
uspto-grants-2009_09
Patent number
US07589116B2

Reaction notes

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