Hydrazine → 4-(4-CHLORO-3,5-DIMETHYL-1H-PYRAZOL-1-YL)ANILINE

HRID 2236494Notes

Reaction equation

HRID 2236494 reaction equation
Cl.[Cl:2][C:3]1[C:4]([CH3:18])=[N:5][N:6]([C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=2)[C:7]=1[CH3:8].NN>CO>[Cl:2][C:3]1[C:4]([CH3:18])=[N:5][N:6]([C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)[C:7]=1[CH3:8]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 68697462HCID 68697462, compound

Product 1

HCID 196165864-(4-CHLORO-3,5-DIMETHYL-1H-PYRAZOL-1-YL)ANILINEYield 104.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Chloro-3,5-dimethyl-1-(4-nitro-phenyl)-1H-pyrazole hydrochloride (450 mg, 1.56 mmol) is dissolved in MeOH (40 mL). To this solution is then added FeCl3.6H2O (24 mg, 0.09 mmol) and active carbon (12 mg, 1 mmol). The suspension is heated to reflux. Hydrazine (2.0 mL) is added, and reflux is continued for 3 h or until TLC detected full conversion. After conversion the mixture is cooled to room temperature, the active carbon is filtered off using celite and the MeOH under reduced pressure. The residue is purified with flash chromatography to provide the 4-(4-Chloro-3,5-dimethyl-pyrazol-1-yl)-phenylamine (360 mg, 91%). MS (ESI): 222, 224 (M+1)+1.

Workup

  1. temperatureThe suspension is heated to reflux
  2. temperaturereflux
  3. filtrationthe active carbon is filtered off
  4. customThe residue is purified with flash chromatography

Sources & evidence

ORD record
ord-452ff9115191478f993d5be03bf9a473
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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