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

HRID 1738616Notes

Reaction equation

HRID 1738616 reaction equation
O.[P].[Cl:3][C:4]1[C:9]([N+:10]([O-])=O)=[CH:8][C:7]([C:13]([F:16])([F:15])[F:14])=[CH:6][C:5]=1[N+:17]([O-])=O>[Pt].O[PH2]=O.C1(C)C=CC=CC=1>[NH2:17][C:5]1[CH:6]=[C:7]([C:13]([F:16])([F:14])[F:15])[CH:8]=[C:9]([NH2:10])[C:4]=1[Cl:3]

Participants

7

Reactant 3

HCID 962WaterHCID 98094-Chloro-3,5-dinitrobenzotrifluorideHCID 5462309Phosphorus

Product 1

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

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 4124402Phosphinic AcidCatalystHCID 1140TolueneSolvent

Procedure

0.48 g of Pt/C catalyst (5%) and 1.5 g of water are placed in a beaker and mixed with 103 mg of aqueous H3PO2 solution (50% by weight, corresponding to 5% by weight phosphorus, based on the catalyst). The mixture is stirred for 10 minutes at room temperature, then 77 mg of vanadylacetyl acetonate VO(acac)2 are added and stirred for a further 5 minutes. 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. stirringstirred for a further 5 minutes
  2. customthe catalyst suspension is flushed in with 4 g of water
  3. customat a temperature of 100° C.
  4. temperaturethe autoclave is cooled
  5. filtrationThe catalyst is filtered off
  6. washwashed with toluene

Sources & evidence

ORD record
ord-bbd889f608cd4b4ea1ad648c75cbbb73
Source dataset
uspto-grants-1999_10
Patent number
US05962741

Reaction notes

Loading…