4-Chloro-3,5-dinitrobenzotrifluoride → 2-Chloro-5-(trifluoromethyl)benzene-1,3-diamine

HRID 1530781Notes

Reaction equation

HRID 1530781 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([C:11]([F:14])([F:13])[F:12])=[CH:4][C:3]=1[N+:15]([O-])=O>C1(C)C=CC=CC=1>[NH2:15][C:3]1[CH:4]=[C:5]([C:11]([F:14])([F:12])[F:13])[CH:6]=[C:7]([NH2:8])[C:2]=1[Cl:1]

Participants

3

Reactant 1

HCID 98094-Chloro-3,5-dinitrobenzotrifluoride

Product 1

HCID 124029942-Chloro-5-(trifluoromethyl)benzene-1,3-diamineYield 95.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

40 g of 4-chloro-3,5-dinitro-benzotrifluoride and 47 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, 29.8 g of 3,5-diamino-4-chloro-benzotrifluoride (yield 95.8% of theory) are obtained. Elementary analysis:

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-bd2165999a854fd481c554940a25c878
Source dataset
uspto-grants-2001_03
Patent number
US06197716B1

Reaction notes

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