3,4-Dichlorobenzotrifluoride → [2-Chloro-5-(trifluoromethyl)phenyl]hydrazine

HRID 2188256Notes

Reaction equation

HRID 2188256 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:6][C:7]=1[Cl:8].O.[NH2:14][NH2:15]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:6][C:7]=1[NH:14][NH2:15].[Cl:8][C:7]1[CH:6]=[CH:5][C:4]([C:9]([F:12])([F:11])[F:10])=[CH:3][C:2]=1[NH:14][NH2:15]

Participants

5

Reactant 2

HCID 94813,4-DichlorobenzotrifluorideHCID 24654Hydrazine hydrate (1:1)

Product 2

HCID 2060249[2-Chloro-5-(trifluoromethyl)phenyl]hydrazineHCID 2736687[2-Chloro-4-(trifluoromethyl)phenyl]hydrazine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 3,4-dichlorobenzotrifluoride (48 g), hydrazine hydrate (65 g) and pyridine (240 g) was stirred and heated at 150° C. for 6 hours in an autoclave at a pressure of 4 bar. The cooled mixture was quenched with sodium hydroxide solution and the organic layer evaporated in vacuo. The residue was dissolved in diethyl ether, washed (water) and the ether evaporated to give 2-chloro-4-trifluoromethylphenylhydrazine and 2-chloro-5-trifluoromethylphenylhydrazine as a 95/5 mixture (36 g),

Workup

  1. customThe cooled mixture was quenched with sodium hydroxide solution
  2. customthe organic layer evaporated in vacuo
  3. dissolutionThe residue was dissolved in diethyl ether
  4. washwashed (water)
  5. customthe ether evaporated

Sources & evidence

ORD record
ord-63687c2795ab47eba8505e66b61fc6b6
Source dataset
uspto-grants-2002_06
Patent number
US06410737B1

Reaction notes

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