1-Chloro-4-(trifluoromethyl)benzene → 4-(Trifluoromethyl)phenylhydrazine

HRID 2188255Notes

Reaction equation

HRID 2188255 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.O.[NH2:13][NH2:14]>N1C=CC=CC=1>[F:9][C:8]([F:11])([F:10])[C:5]1[CH:6]=[CH:7][C:2]([NH:13][NH2:14])=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 73941-Chloro-4-(trifluoromethyl)benzeneHCID 24654Hydrazine hydrate (1:1)

Product 1

HCID 1362004-(Trifluoromethyl)phenylhydrazineYield 20%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 4-chlorobenzotrifluoride (1.08 g), hydrazine hydrate (1.8 g, 6 molar equivalents) and pyridine (5 ml) was heated in an autoclave (purged with argon) for 6 hours at 180° C. The mixture was cooled, the excess hydrazine decanted and the organic phase evaporated in vacuo. The residue was crystallised from petroleum ether to give the title compound in 20% yield. It was shown that 20% of the starting material had been consumed, thus indicating that the reaction had occurred with high selectivity.

Workup

  1. temperatureThe mixture was cooled
  2. customthe excess hydrazine decanted
  3. customthe organic phase evaporated in vacuo
  4. customThe residue was crystallised from petroleum ether

Sources & evidence

ORD record
ord-c1a8c17a6cbf4691b7b37d844a28a21d
Source dataset
uspto-grants-2002_06
Patent number
US06410737B1

Reaction notes

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