1-Iodo-4-nitro-2-(trifluoromethyl)benzene → 4-Iodo-3-(trifluoromethyl)aniline

HRID 396219Notes

Reaction equation

HRID 396219 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12]>[Ni].CO>[NH2:8][C:5]1[CH:4]=[C:3]([C:11]([F:14])([F:12])[F:13])[C:2]([I:1])=[CH:7][CH:6]=1

Participants

4

Reactant 1

HCID 192617781-Iodo-4-nitro-2-(trifluoromethyl)benzene

Product 1

HCID 230036244-Iodo-3-(trifluoromethyl)aniline

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

In the presence of 1.7 g of Raney nickel, 8.6 g (27 mmol) of 4-iodo-3-trifluoromethyl-nitro-benzene are hydrogenated in 170 ml of methanol. The reaction mixture is filtered over Celite. Concentration of the filtrate by evaporation yields the oily title compound, which slowly crystallises when left to stand: 1H NMR (CDCl3) 7.63 (d, 1H), 6.98 (d, 1H), 6.54 (dd, 1H), 5.75 (s, H2N); FAB-MS (M+H)+=288.

Workup

  1. filtrationThe reaction mixture is filtered over Celite
  2. customConcentration of the filtrate by evaporation

Sources & evidence

ORD record
ord-ed12089089dc4fa88d414d1b36a86651
Source dataset
uspto-grants-2003_08
Patent number
US06608071B2

Reaction notes

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