Phenylhydrazine hydrochloride → 1-phenyl-3-(1-(trifluoromethyl)cyclopropyl)-1H-pyrazol-5-amine

HRID 1917888Notes

Reaction equation

HRID 1917888 reaction equation
O=[C:2]([C:6]1([C:9]([F:12])([F:11])[F:10])[CH2:8][CH2:7]1)[CH2:3][C:4]#[N:5].Cl.[C:14]1([NH:20][NH2:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CCO.O>[C:14]1([N:20]2[C:4]([NH2:5])=[CH:3][C:2]([C:6]3([C:9]([F:10])([F:11])[F:12])[CH2:8][CH2:7]3)=[N:21]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 60962Phenylhydrazine hydrochlorideHCID 668764113-Oxo-3-(1-(trifluoromethyl)cyclopropyl)propanenitrile

Product 1

HCID 668765051-phenyl-3-(1-(trifluoromethyl)cyclopropyl)-1H-pyrazol-5-amineYield 43.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
90 °C

Procedure

To 3-oxo-3-(1-(trifluoromethyl)cyclopropyl)propanenitrile (230 mg, 1.3 mmol) in EtOH (5 mL, 200 proof) was added H2O (3.7 mL), 1NaOH(aq) (1.3 mL), and phenylhydrazine hydrochloride (188 mg, 1.3 mmol) and the mixture heated at 90° C. overnight. After cooling to room temperature, the mixture was diluted with H2O, extracted with EtOAc, the org layer concentrated in vacuo, and purified by column chromatography (5-25% EtOAc/hexanes) to give 1-phenyl-3-(1-(trifluoromethyl)cyclopropyl)-1H-pyrazol-5-amine (150 mg, 0.56 mmol, 43%). LC-MS (ESI) m/z 268 (M+H)+.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with EtOAc
  3. concentrationthe org layer concentrated in vacuo
  4. custompurified by column chromatography (5-25% EtOAc/hexanes)

Sources & evidence

ORD record
ord-8d96f4eef52e4f47affe6d344f222609
Source dataset
uspto-grants-2013_12
Patent number
US08618289B2

Reaction notes

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