Hydrochloric Acid → 3-(4-methoxy-3-methyl-phenyl)-1-methyl-5-trifluoromethyl-1H-pyrazole

HRID 628523Notes

Reaction equation

HRID 628523 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:10][C:11]([C:16]([F:19])([F:18])[F:17])(O)[N:12]([CH3:14])[N:13]=2)=[CH:5][C:4]=1[CH3:20].Cl>O1CCCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]([C:16]([F:19])([F:17])[F:18])[N:12]([CH3:14])[N:13]=2)=[CH:5][C:4]=1[CH3:20]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 1180013235-(4-methoxy-3-methyl-phenyl)-2-methyl-3-trifluoromethyl-3,4-dihydro-2H-pyrazol-3-ol

Product 1

HCID 1180013303-(4-methoxy-3-methyl-phenyl)-1-methyl-5-trifluoromethyl-1H-pyrazoleYield 102%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-(4-methoxy-3-methyl-phenyl)-2-methyl-3-trifluoromethyl-3,4-dihydro-2H-pyrazol-3-ol (described in Reference preparation example 77) 2.3 g, 6N aqueous hydrochloric acid solution 4 ml and tetrahydrofuran 30 ml was stirred with heating under reflux for two hours. The reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium carbonate solution and saturated saline. The organic layer was dried over anhydrous magnesium sulfate, and was then concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to give 3-(4-methoxy-3-methyl-phenyl)-1-methyl-5-trifluoromethyl-1H-pyrazole 2.2 g.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for two hours
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated aqueous sodium carbonate solution and saturated saline
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationwas then concentrated under reduced pressure

Sources & evidence

ORD record
ord-0b90586a364d4d939c030d2a78021562
Source dataset
uspto-grants-2016_04
Patent number
US09314023B2

Reaction notes

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