1,2-Dichloro-4-nitrobenzene → 3,4-Dichloroaniline

HRID 1530782Notes

Reaction equation

HRID 1530782 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N+:9]([O-])=O)[CH:5]=[CH:6][C:7]=1[Cl:8]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[Cl:8])[NH2:9]

Participants

3

Reactant 1

HCID 74431,2-Dichloro-4-nitrobenzene

Product 1

HCID 72573,4-DichloroanilineYield 96.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

22.1 g of 3,4-dichloro-nitrobenzene and 70 g of toluene are placed in an agitator autoclave, and the catalyst suspension is flushed in with 4 g of water. Hydrogenation subsequently takes place at a temperature of 100° C. and at a hydrogen pressure of 5 bar. When the hydrogen uptake is complete, the autoclave is cooled and rendered inert with nitrogen. The catalyst is filtered off and washed with toluene. After working up by distillation, 18.0 g of 3,4-dichloroaniline (yield 96.8% of theory) are obtained.

Workup

  1. customthe catalyst suspension is flushed in with 4 g of water
  2. customat a temperature of 100° C.
  3. temperaturethe autoclave is cooled
  4. filtrationThe catalyst is filtered off
  5. washwashed with toluene

Sources & evidence

ORD record
ord-4360bd5036894679bf553ffe8b139174
Source dataset
uspto-grants-2001_03
Patent number
US06197716B1

Reaction notes

Loading…