Phenylhydrazine hydrochloride → 3-(1,3-difluoro-2-methylpropan-2-yl)-1-phenyl-1H-pyrazol-5-amine

HRID 1917934Notes

Reaction equation

HRID 1917934 reaction equation
[F:1][CH2:2][C:3]([CH2:10][F:11])([CH3:9])[C:4](=O)[CH2:5][C:6]#[N:7].Cl.[C:13]1([NH:19][NH2:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CCO>[F:1][CH2:2][C:3]([C:4]1[CH:5]=[C:6]([NH2:7])[N:19]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:20]=1)([CH3:9])[CH2:10][F:11]

Participants

4

Reactant 2

HCID 60962Phenylhydrazine hydrochlorideHCID 866535185-Fluoro-4-(fluoromethyl)-4-methyl-3-oxopentanenitrile

Product 1

HCID 668762133-(1,3-difluoro-2-methylpropan-2-yl)-1-phenyl-1H-pyrazol-5-amineYield 59.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
95 °C

Procedure

According to the procedure described in Example 161B Step 2, 5-fluoro-4-(fluoromethyl)-4-methyl-3-oxopentanenitrile (0.81 g, 5 mmol) and phenylhydrazine hydrochloride (0.868 g, 14 mmol) in EtOH were heated at 95° C. for 2 hours, to afford 3-(1,3-difluoro-2-methylpropan-2-yl)-1-phenyl-1H-pyrazol-5-amine as solid (0.75 g, 52%). LC-MS (ESI) m/z 252 (M+H)+.

Sources & evidence

ORD record
ord-2d3508529299457aa0e52cba282b9b69
Source dataset
uspto-grants-2013_12
Patent number
US08618289B2

Reaction notes

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