3-Chloro-5-nitrobenzotrifluoride → 3-Chloro-5-(trifluoromethyl)aniline

HRID 49217Notes

Reaction equation

HRID 49217 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:5]=[C:6]([N+:8]([O-])=O)[CH:7]=1>CO.[Ni]>[NH2:8][C:6]1[CH:7]=[C:2]([Cl:1])[CH:3]=[C:4]([C:11]([F:12])([F:13])[F:14])[CH:5]=1

Participants

4

Reactant 1

HCID 502553-Chloro-5-nitrobenzotrifluoride

Product 1

HCID 30179333-Chloro-5-(trifluoromethyl)aniline

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

92 g (0.408 mol) of 5-chloro-3-trifluoromethyl-nitrobenzene in 1 l of methanol are hydrogenated in the presence of 10.17 g of Raney nickel. The reaction mixture is filtered through Celite/activated carbon and the residue washed with methanol. Concentration of the filtrate by evaporation yields the oily 5-amino-3-chloro-benzotrifluoride; 1H-NMR (DMSO-d6) δ6.80 (m, 3H), 5.92 (s, H2N).

Workup

  1. filtrationThe reaction mixture is filtered through Celite/activated carbon
  2. washthe residue washed with methanol
  3. customConcentration of the filtrate by evaporation

Sources & evidence

ORD record
ord-990f9d25dd51402ba6bc222c113bad97
Source dataset
uspto-grants-2004_03
Patent number
US06706731B2

Reaction notes

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