Methylhydrazine → 5-(4-methoxy-2,5-dimethyl-phenyl)-2-methyl-3-trifluoromethyl-3,4-dihydro-2H-pyrazole-3-ol

HRID 628528Notes

Reaction equation

HRID 628528 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3](=[O:17])[CH2:4][C:5]([C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([O:14][CH3:15])=[CH:9][C:8]=1[CH3:16])=O.[CH3:20][NH:21][NH2:22]>C(O)C>[CH3:15][O:14][C:10]1[C:11]([CH3:13])=[CH:12][C:7]([C:5]2[CH2:4][C:3]([C:2]([F:19])([F:18])[F:1])([OH:17])[N:21]([CH3:20])[N:22]=2)=[C:8]([CH3:16])[CH:9]=1.[CH3:15][O:14][C:10]1[C:11]([CH3:13])=[CH:12][C:7]([C:5]2[N:21]([CH3:20])[N:22]=[C:3]([C:2]([F:19])([F:18])[F:1])[CH:4]=2)=[C:8]([CH3:16])[CH:9]=1

Participants

5

Reactant 2

HCID 6061MethylhydrazineHCID 985795504,4,4-Trifluoro-1-(4-methoxy-2,5-dimethyl-phenyl)-butane-1,3-dione

Product 2

HCID 1182363955-(4-methoxy-2,5-dimethyl-phenyl)-2-methyl-3-trifluoromethyl-3,4-dihydro-2H-pyrazole-3-olHCID 1182364825-(4-methoxy-2,5-dimethyl-phenyl)-1-methyl-3-trifluoromethyl-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

At 0° C., to a mixture of 4,4,4-trifluoro-1-(4-methoxy-2,5-dimethyl-phenyl)-butane-1,3-dione (described in Reference Preparation example 83) 6.8 g and ethanol 100 ml was added methyl hydrazine 1.7 g. The resulting mixture was raised to room temperature and was stirred for one hour. The reaction mixture was concentrated under reduced pressure and the resulting residue was subjected to a silica gel column chromatography to give 5-(4-methoxy-2,5-dimethyl-phenyl)-2-methyl-3-trifluoromethyl-3,4-dihydro-2H-pyrazole-3-ol 3.2 g and 5-(4-methoxy-2,5-dimethyl-phenyl)-1-methyl-3-trifluoromethyl-1H-pyrazole 3 g.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7707dc037b63455eb7b0a058c33de0f0
Source dataset
uspto-grants-2016_04
Patent number
US09314023B2

Reaction notes

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