3-Ethoxy-2-propenenitrile → 1-(4-FLUORO-PHENYL)-1H-PYRAZOL-3-AMINE

HRID 1260310Notes

Reaction equation

HRID 1260310 reaction equation
CC(C)([O-])C.[K+].Cl.[F:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][NH2:16])=[CH:11][CH:10]=1.C(O[CH:20]=[CH:21][C:22]#[N:23])C>C(O)(C)(C)C>[F:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH:20]=[CH:21][C:22]([NH2:23])=[N:16]2)=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 436013-Ethoxy-2-propenenitrileHCID 699814-Fluorophenylhydrazine hydrochlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 136269441-(4-FLUORO-PHENYL)-1H-PYRAZOL-3-AMINEYield 44%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent2×

Procedure

To a hot solution of potassium tert-butoxide (2.54 g, 23 mmol) in tert-butanol (30 ml) was added 4-fluorophenylhydrazine hydrochloride (1.67 g, 10 mmol). After cooling to ambient temperature, a solution of 3-ethoxyacrylonitrile (1.0 g, 10 mmol) in tert-butanol (5 ml) was added and the mixture was refluxed for 3 h. After cooling to ambient temperature, the solvent was evaporated. The residue was dissolved in ethyl acetate and extracted with water. The organic phases were combined, dried and evaporated. Silica gel chromatography using a heptane/ethyl acetate gradient yielded the amine as orange solid (0.78 g, 42%).

Workup

  1. temperaturethe mixture was refluxed for 3 h
  2. temperatureAfter cooling to ambient temperature
  3. customthe solvent was evaporated
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. extractionextracted with water
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-d2cd1d3783a4494295c35788f6a43f8a
Source dataset
uspto-grants-2013_06
Patent number
US08470820B2

Reaction notes

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