1,3,5-Trichlorobenzene → 3,5-Dichlorophenylhydrazine

HRID 1635692

Reaction equation

HRID 1635692 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[CH:5]=[C:4]([Cl:9])[CH:3]=1.O.[NH2:11][NH2:12]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([NH:11][NH2:12])[CH:5]=[C:4]([Cl:9])[CH:3]=1

Participants

4

Reactant 2

HCID 79501,3,5-TrichlorobenzeneHCID 24654Hydrazine hydrate (1:1)

Product 1

HCID 6004693,5-DichlorophenylhydrazineYield 60%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 1,3,5-trichlorobenzene (2.53 g), hydrazine hydrate (3.48 g, 5 molar equivalents) and pyridine (12 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 to give the title compound in 60% yield. It was shown that 65% 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

Sources & evidence

ORD record
ord-3e6a2dccd2424f91bb0356d383f5ee0e
Source dataset
uspto-grants-2003_01
Patent number
US06509503B1

Linked notes

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