1-(4-Fluorophenyl)-5-(3-(trifluoromethoxy)phenyl)-4,5-dihydro-1H-pyrazol-3-ylamine → 1-(4-Fluorophenyl)-5-(3-(trifluoromethoxy)phenyl)-1H-pyrazol-3-ylamine

HRID 83494Notes

Reaction equation

HRID 83494 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19][C:20]([F:23])([F:22])[F:21])[CH:14]=3)[CH2:11][C:10]([NH2:24])=[N:9]2)=[CH:4][CH:3]=1>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19][C:20]([F:21])([F:23])[F:22])[CH:14]=3)=[CH:11][C:10]([NH2:24])=[N:9]2)=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 712877431-(4-Fluorophenyl)-5-(3-(trifluoromethoxy)phenyl)-4,5-dihydro-1H-pyrazol-3-ylamine

Product 1

HCID 712877381-(4-Fluorophenyl)-5-(3-(trifluoromethoxy)phenyl)-1H-pyrazol-3-ylamineYield 50.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 1-(4-fluorophenyl)-5-(3-(trifluoromethoxy)phenyl)-4,5-dihydro-1H-pyrazol-3-ylamine (1.29 g) in toluene (10 ml) was added activated carbon (pH5 to 8, 0.64 g), and the mixture was stirred for 2 hours under oxygen atmosphere under cooling to reflux. After cooling to room temperature, the activated carbon was filtered off through Celite eluting with ethyl acetate. This filtrate was concentrated under reduced pressure. To the resulting residue, a mixed solvent of diisopropyl ether/n-hexane was added and the mixture was stirred at room temperature. The insoluble substance was collected by filtration, and then dried under reduced pressure to give the titled compound (652 mg).

Workup

  1. temperatureunder cooling
  2. temperatureto reflux
  3. filtrationthe activated carbon was filtered off through Celite
  4. washeluting with ethyl acetate
  5. concentrationThis filtrate was concentrated under reduced pressure
  6. additionTo the resulting residue, a mixed solvent of diisopropyl ether/n-hexane was added
  7. stirringthe mixture was stirred at room temperature
  8. filtrationThe insoluble substance was collected by filtration
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-1451ea0a4c834f8fbf057590cca2cec7
Source dataset
uspto-grants-2014_09
Patent number
US08846746B2

Reaction notes

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