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

HRID 871516Notes

Reaction equation

HRID 871516 reaction equation
[F:1][C:2]([F:9])([F:8])[C:3](=O)[CH2:4][C:5]#[N:6].Cl.[C:11]1([NH:17][NH2:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>CCO>[C:11]1([N:17]2[C:5]([NH2:6])=[CH:4][C:3]([C:2]([F:9])([F:8])[F:1])=[N:18]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 60962Phenylhydrazine hydrochlorideHCID 138435404,4,4-Trifluoro-3-oxobutanenitrile

Product 1

HCID 431589511-phenyl-3-(trifluoromethyl)-1H-pyrazol-5-amineYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4,4,4-trifluoro-3-oxobutanenitrile (2.056 g, 15 mmol) and phenylhydrazine hydrochloride (2.169 g, 15 mmol) in EtOH was heated at 90° C. for 8 hours. The reaction was quenched with water, basified with saturated NaHCO3 solution, and extracted with CH2Cl2. Extracts were dried over MgSO4, concentrated under reduced pressure, and dried under vacuum to afford 1-phenyl-3-(trifluoromethyl)-1H-pyrazol-5-amine as yellow solid (3.089 g, 91%). 1H NMR (300 MHz, CDCl3) δ 7.54 (m, 5H), 5.85 (s, 1H), 3.95 (br, 2H); LC-MS (ESI) m/z 228 (M+H)+.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with CH2Cl2
  3. dry with materialExtracts were dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customdried under vacuum

Sources & evidence

ORD record
ord-6e46e8f323814271aad5712cfef73a22
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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