(4-Methylphenyl)hydrazine → 5-Pentafluoroethyl-2-p-tolyl-2H-pyrazol-3-ylamine

HRID 729596Notes

Reaction equation

HRID 729596 reaction equation
[F:1][C:2]([F:12])([C:8]([F:11])([F:10])[F:9])[C:3](=O)[CH2:4][C:5]#[N:6].[C:13]1([CH3:21])[CH:18]=[CH:17][C:16]([NH:19][NH2:20])=[CH:15][CH:14]=1>C(O)C>[F:1][C:2]([F:12])([C:3]1[CH:4]=[C:5]([NH2:6])[N:19]([C:16]2[CH:17]=[CH:18][C:13]([CH3:21])=[CH:14][CH:15]=2)[N:20]=1)[C:8]([F:9])([F:11])[F:10]

Participants

4

Reactant 2

HCID 10875(4-Methylphenyl)hydrazineHCID 156138214,4,5,5,5-Pentafluoro-3-oxopentanenitrile

Product 1

HCID 578328135-Pentafluoroethyl-2-p-tolyl-2H-pyrazol-3-ylamineYield 52%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Heat a mixture of 4,4,5,5,5-pentafluoro-3-oxo-pentanenitrile (4 g, 21.4 mmol) and p-tolyl-hydrazine (10 g, 64.1 mmol) in ethanol (20 mL) to 95° C. in a sealed tube apparatus for 15 hours. After cooling to room temperature, remove the solvent under reduced pressure to give a brown residue. Subject residue to silica gel chromatography eluting with ethyl acetate and hexanes to give the title compound (3.24 g, 52% yield, ES+(m/z) 292.1 [M+H]).

Workup

  1. temperatureHeat
  2. customremove the solvent under reduced pressure
  3. customto give a brown residue
  4. washSubject residue to silica gel chromatography eluting with ethyl acetate and hexanes

Sources & evidence

ORD record
ord-68bcfd48251b4a368446c3d13389209c
Source dataset
uspto-grants-2009_09
Patent number
US07582638B2

Reaction notes

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