Hydrochloric Acid → HCID 68677988, compound

HRID 1993924Notes

Reaction equation

HRID 1993924 reaction equation
CO[C:3](=[O:16])[CH2:4][C:5](=O)[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=1.[F:17][C:18]1[CH:23]=[CH:22][C:21]([NH:24][NH2:25])=[CH:20][CH:19]=1.Cl.CCOC(C)=O>C(O)(=O)C.O>[F:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]2[C:3](=[O:16])[CH2:4][C:5]([CH2:6][CH2:7][C:8]3[CH:9]=[CH:10][C:11]([F:14])=[CH:12][CH:13]=3)=[N:25]2)=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 69982(4-Fluorophenyl)hydrazineHCID 66789979500367-64-6

Product 1

HCID 68677988HCID 68677988, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a solution of 5-(4-fluoro-phenyl)-3-oxo-pentanoic acid methyl ester (0.43 g) in acetic acid (5 mL) in a sealable tube was added 4-fluorophenylhydrazine.HCl (0.31 g). The reaction vessel was sealed and immersed into an oil bath at 100° C. for 18 hours. The reaction vessel was cooled to ambient temperature, opened and the contents were poured onto a mixture of EtOAc and water. The aqueous phase was extracted with EtOAc and the combined organic phases were washed with water and dried over sodium sulfate. Filtration and evaporation of the volatiles in vacuo afforded a crude crystalline material. The crude product was washed with ether to afford the desired 2-(4-fluoro-phenyl)-5-[2-(4-fluoro-phenyl)-ethyl]-2,4-dihydro-pyrazol-3-one (0.37 g) as a beige crystalline solid. MS (ESI+): 301.1 [M+H]+).

Workup

  1. customThe reaction vessel was sealed
  2. extractionThe aqueous phase was extracted with EtOAc
  3. washthe combined organic phases were washed with water
  4. dry with materialdried over sodium sulfate
  5. filtrationFiltration and evaporation of the volatiles in vacuo
  6. customafforded a crude crystalline material
  7. washThe crude product was washed with ether

Sources & evidence

ORD record
ord-00157bec1a6a4e4b8037323192c2c75b
Source dataset
uspto-grants-2010_01
Patent number
US07652057B2

Reaction notes

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