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

HRID 396218Notes

Reaction equation

HRID 396218 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>[Ni].CO>[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

In the presence of 10.17 g of Raney nickel, 92 g (0.408 mol) of 5-chloro-3-trifluoromethyl-nitrobenzene are hydrogenated in 1 liter of methanol. The reaction mixture is filtered over Celite/activated carbon and the residue is washed with methanol. Concentration of the filtrate by evaporation yields the oily title compound: 1H-NMR (DMSO-d6) 6.80 (m, 3H), 5.92 (s, H2N); FAB-MS (M+H)+=196.

Workup

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

Sources & evidence

ORD record
ord-cc20a5945ffa49ba92a742b02de78dd3
Source dataset
uspto-grants-2003_08
Patent number
US06608071B2

Reaction notes

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