Phenylhydrazine hydrochloride → ethyl 1-phenyl-5-(2,4,5-trifluorophenyl)-1H-pyrazole-4-carboxylate

HRID 402759

Reaction equation

HRID 402759 reaction equation
O=[C:2]([C:9]1[CH:14]=[C:13]([F:15])[C:12]([F:16])=[CH:11][C:10]=1[F:17])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].COC(OC)[N:21]([CH3:23])C.Cl.[C:27]1([NH:33]N)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(O)C.CCOC(C)=O>[C:27]1([N:33]2[C:2]([C:9]3[CH:14]=[C:13]([F:15])[C:12]([F:16])=[CH:11][C:10]=3[F:17])=[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH:23]=[N:21]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 3

HCID 60962Phenylhydrazine hydrochlorideHCID 78373Dimethylformamide dimethyl acetalHCID 2758933Ethyl 2,4,5-trifluorobenzoylacetate

Product 1

HCID 86685264ethyl 1-phenyl-5-(2,4,5-trifluorophenyl)-1H-pyrazole-4-carboxylate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of ethyl 3-oxo-3-(2,4,5-trifluorophenyl)propanoate (0.326 g, 1.32 mmol) and N,N-dimethyformamide dimethyl acetal in ethanol (5 mL) was heated in a 90° C. oil bath for 3 hours. Upon removal of the volatiles, the residue was dissolved in EtOH (3 mL) and phenylhydrazine hydrochloride salt (191 mg, 1.324 mmol) was added. The mixture was then heated at reflux for 6 hours. The reaction was cooled and diluted with EtOAc and the organic layer was washed with NaHCO3 and brine. The organic phase was dried with Na2SO4, filtered and concentrated to afford the title compound as oil.

Workup

  1. customUpon removal of the volatiles
  2. dissolutionthe residue was dissolved in EtOH (3 mL)
  3. temperatureThe mixture was then heated
  4. temperatureat reflux for 6 hours
  5. temperatureThe reaction was cooled
  6. washthe organic layer was washed with NaHCO3 and brine
  7. dry with materialThe organic phase was dried with Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-2c3f4e2ed52c445c8ea94ce06b9794be
Source dataset
uspto-grants-2014_06
Patent number
US08742110B2

Linked notes

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