Hydrochloric Acid → HCID 178492075, compound

HRID 1289840Notes

Reaction equation

HRID 1289840 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3](=O)[CH2:4][C:5]([O:7]CC)=O.Cl.[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][NH2:23])=[CH:18][CH:17]=1.Cl>CO>[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]2[C:5]([OH:7])=[CH:4][C:3]([C:2]([F:1])([F:11])[F:12])=[N:23]2)=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 67793Ethyl 4,4,4-trifluoroacetoacetateHCID 27239044-Methoxyphenylhydrazine hydrochloride

Product 1

HCID 178492075HCID 178492075, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 5 g (27.2 mmol) of ethyl trifluoroacetoacetate, 4.76 g (27.2 mmol) of 4-methoxyphenylhydrazine hydrochloride, and 0.5 ml of conc. HCl in 60 ml of methanol was refluxed with stirring for 22 hours. After removing methanol in vacuo, toluene was added and the resulting mixture was refluxed for 20 hours and cooled. The mixture was diluted with aqueous sodium bicarbonate solution, extracted with ethyl acetate, and the organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was recrystallized from methylene chloride/hexane and ethyl acetate/hexane to afford 3.7 g (53%) of 1-(4-methoxyphenyl)-3-trifluoromethyl-5-hydroxypyrazole as a tan solid.

Workup

  1. temperaturewas refluxed
  2. customAfter removing methanol in vacuo, toluene
  3. additionwas added
  4. temperaturethe resulting mixture was refluxed for 20 hours
  5. temperaturecooled
  6. additionThe mixture was diluted with aqueous sodium bicarbonate solution
  7. extractionextracted with ethyl acetate
  8. dry with materialthe organic layer was dried over sodium sulfate
  9. concentrationconcentrated in vacuo
  10. customThe residue was recrystallized from methylene chloride/hexane and ethyl acetate/hexane

Sources & evidence

ORD record
ord-9fec037b9b3f448faa894baad5833020
Source dataset
uspto-grants-1998_05
Patent number
US05750550

Reaction notes

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