1,1,1,5,5,6,6,6-Octafluoro-2,4-hexanedione → 2-(3-methyl-4-nitro-phenyl)-5-pentafluoroethyl-3-trifluoromethyl-3,4-dihydro-2H-pyrazol-3-ol

HRID 2243264Notes

Reaction equation

HRID 2243264 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:11][NH2:12])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[F:13][C:14]([F:28])([F:27])[C:15](=[O:26])[CH2:16][C:17](=O)[C:18]([F:24])([F:23])[C:19]([F:22])([F:21])[F:20]>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:3]=[C:4]([N:11]2[C:15]([C:14]([F:28])([F:27])[F:13])=[CH:16][C:17]([C:18]([F:23])([F:24])[C:19]([F:20])([F:21])[F:22])=[N:12]2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[CH3:1][C:2]1[CH:3]=[C:4]([N:11]2[C:15]([C:14]([F:28])([F:27])[F:13])([OH:26])[CH2:16][C:17]([C:18]([F:23])([F:24])[C:19]([F:20])([F:21])[F:22])=[N:12]2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]

Participants

5

Reactant 2

HCID 1407641,1,1,5,5,6,6,6-Octafluoro-2,4-hexanedioneHCID 13158578(3-Methyl-4-nitrophenyl)hydrazine

Product 2

HCID 592103972-(3-methyl-4-nitro-phenyl)-5-pentafluoroethyl-3-trifluoromethyl-3,4-dihydro-2H-pyrazol-3-olHCID 592104211-(3-methyl-4-nitro-phenyl)-3-pentafluoroethyl-5-trifluoromethyl-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

(3-Methyl-4-nitro-phenyl)-hydrazine (2.0 g) and 1,1,1,5,5,6,6,6-octafluoro-2,4-hexanedione (3.1 g) were dissolved in toluene and the solution was refluxed for 6 hours. After cooling, the solvent was distilled off and the obtained residue was purified by silica gel column chromatography to obtain 1-(3-methyl-4-nitro-phenyl)-3-pentafluoroethyl-5-trifluoromethyl-1H-pyrazole (IX-3) (3.0 g) and 2-(3-methyl-4-nitro-phenyl)-5-pentafluoroethyl-3-trifluoromethyl-3,4-dihydro-2H-pyrazol-3-ol (IX-4) (0.5 g), respectively.

Workup

  1. temperaturethe solution was refluxed for 6 hours
  2. temperatureAfter cooling
  3. distillationthe solvent was distilled off
  4. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b9e65915bbda42ae80e60d6fb993e08e
Source dataset
uspto-grants-2010_03
Patent number
US07674807B2

Reaction notes

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