Acetic Acid → 1-(3-Aminophenyl)-5-phenyl-3-(trifluoromethyl)pyrazole

HRID 644473Notes

Reaction equation

HRID 644473 reaction equation
C(O)(=O)C.[N+:5]([C:8]1[CH:9]=[C:10]([N:14]2[C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:17][C:16]([C:25]([F:28])([F:27])[F:26])=[N:15]2)[CH:11]=[CH:12][CH:13]=1)([O-])=O>[Pd].C(O)C>[NH2:5][C:8]1[CH:9]=[C:10]([N:14]2[C:18]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:17][C:16]([C:25]([F:28])([F:27])[F:26])=[N:15]2)[CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 230699751-(3-Nitrophenyl)-5-phenyl-3-(trifluoromethyl)pyrazole

Product 1

HCID 230699491-(3-Aminophenyl)-5-phenyl-3-(trifluoromethyl)pyrazoleYield 91.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Acetic acid (3 mL) and ethanol (2 mL) were added to 1-(3-nitrophenyl)-5-phenyl-3-(trifluoromethyl)pyrazole (0.59 g, 1.77 mmol) and 5% palladium on carbon (0.06 g), and the mixture was hydrogenated at room temperature for 2 hours under hydrogen atmosphere. After the insoluble matter was filtered off, the residue obtained by evaporation under reduced pressure was purified by column chromatography on silica gel (n-hexane:ethyl acetate=2:1) to give the title compound (491.1 mg, 91.4%) as a white solid.

Workup

  1. filtrationAfter the insoluble matter was filtered off
  2. customthe residue obtained by evaporation under reduced pressure
  3. customwas purified by column chromatography on silica gel (n-hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-b0795d965ff043ff9ce67637b0ecb623
Source dataset
uspto-grants-2010_04
Patent number
US07700655B2

Reaction notes

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