Acetic Acid → 2-(5-Methyl-3-trifluoromethyl-1H-pyrazol-1-yl)phenol

HRID 337332

Reaction equation

HRID 337332 reaction equation
Cl.C[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][NH2:11].C(O)(=O)C.[F:16][C:17]([F:25])([F:24])[C:18](=O)[CH2:19][C:20](=O)[CH3:21]>COCCO>[CH3:21][C:20]1[N:10]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[OH:3])[N:11]=[C:18]([C:17]([F:25])([F:24])[F:16])[CH:19]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 739431,1,1-Trifluoro-2,4-pentanedioneHCID 28494452-Methoxyphenylhydrazine Hydrochloride

Product 1

HCID 601433782-(5-Methyl-3-trifluoromethyl-1H-pyrazol-1-yl)phenol

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

300 mg of 2-methoxyphenyl hydrazine hydrochloride was dissolved in 1.3 ml of 2-methoxyethanol, and 2.5 ml of acetic acid and 208 μl of 1,1,1-trifluoro-2,4-pentanedione were added and heated at reflux for 1 hour and 40 minutes. The solvent was distilled off under reduced pressure, and 50 ml of ethyl acetate was added, and the organic layer was washed with 50 ml of a saturated sodium bicarbonate solution and 50 ml of saturated saline and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to yield 485.6 mg of the title compound.

Workup

  1. temperatureheated
  2. temperatureat reflux for 1 hour and 40 minutes
  3. distillationThe solvent was distilled off under reduced pressure, and 50 ml of ethyl acetate
  4. additionwas added
  5. washthe organic layer was washed with 50 ml of a saturated sodium bicarbonate solution and 50 ml of saturated saline
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-bbebde9491ce4d5094a0638d627e45e7
Source dataset
uspto-grants-2014_11
Patent number
US08889727B2

Linked notes

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