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

HRID 628522Notes

Reaction equation

HRID 628522 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3](=[O:16])[CH2:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([CH3:15])[CH:8]=1)=O.[CH3:19][NH:20][NH2:21]>C(O)C>[CH3:14][O:13][C:10]1[CH:11]=[CH:12][C:7]([C:5]2[CH2:4][C:3]([C:2]([F:18])([F:17])[F:1])([OH:16])[N:20]([CH3:19])[N:21]=2)=[CH:8][C:9]=1[CH3:15].[CH3:14][O:13][C:10]1[CH:11]=[CH:12][C:7]([C:5]2[N:20]([CH3:19])[N:21]=[C:3]([C:2]([F:18])([F:17])[F:1])[CH:4]=2)=[CH:8][C:9]=1[CH3:15]

Participants

5

Reactant 2

HCID 6061MethylhydrazineHCID 113912984,4,4-Trifluoro-1-(3-methyl-4-methoxylphenyl)-1,3-butanedione

Product 2

HCID 1180013235-(4-methoxy-3-methyl-phenyl)-2-methyl-3-trifluoromethyl-3,4-dihydro-2H-pyrazol-3-olHCID 1182364545-(4-methoxy-3-methyl-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-3-methyl-phenyl)-butane-1,3-dione (described in Reference Preparation example 76) 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-3-methyl-phenyl)-2-methyl-3-trifluoromethyl-3,4-dihydro-2H-pyrazol-3-ol 3.2 g and 5-(4-methoxy-3-methyl-phenyl)-1-methyl-3-trifluoromethyl-1H-pyrazole 2 g.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-87660aaa554a4954a7feac2a453b3241
Source dataset
uspto-grants-2016_04
Patent number
US09314023B2

Reaction notes

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