Hydrochloric Acid → 1-(3-Nitrophenyl)-5-phenyl-3-(trifluoromethyl)pyrazole

HRID 644472Notes

Reaction equation

HRID 644472 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3](=O)[CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=O.Cl.[N+:17]([C:20]1[CH:21]=[C:22]([NH:26][NH2:27])[CH:23]=[CH:24][CH:25]=1)([O-:19])=[O:18].Cl.C(O)C>O>[N+:17]([C:20]1[CH:21]=[C:22]([N:26]2[C:5]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)=[CH:4][C:3]([C:2]([F:15])([F:14])[F:1])=[N:27]2)[CH:23]=[CH:24][CH:25]=1)([O-:19])=[O:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 675894,4,4-Trifluoro-1-phenyl-1,3-butanedioneHCID 54642853-Nitrophenylhydrazinium(1+) chloride

Product 1

HCID 230699751-(3-Nitrophenyl)-5-phenyl-3-(trifluoromethyl)pyrazoleYield 94.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4,4,4-trifluoro-1-phenyl-1,3-butanedione (432.3 mg, 2 mmol), 3-nitrophenylhydrazine hydrochloride (379.2 mg, 2 mmol), concentrated hydrochloric acid (0.2 mL) and ethanol (8 mL) was reflued for 2 hours. After the reaction mixture was cooled to room temperature, it was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water and brine, and dried over anhydrous sodium sulfate. The residue obtained by evaporation under reduced pressure was purified by column chromatography on silica gel (n-hexane:ethyl acetate=4:1→3:1) to give the title compound (631.5 mg, 94.7%) as a light yellowish white powder.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe residue obtained by evaporation under reduced pressure
  5. customwas purified by column chromatography on silica gel (n-hexane:ethyl acetate=4:1→3:1)

Sources & evidence

ORD record
ord-05804e303a8f49f492eddac5d5740752
Source dataset
uspto-grants-2010_04
Patent number
US07700655B2

Reaction notes

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