5-Amino-2-fluoro-4-nitrobenzotrifluoride → 4-Fluoro-5-(trifluoromethyl)benzene-1,2-diamine

HRID 53790Notes

Reaction equation

HRID 53790 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:12]([F:15])([F:14])[F:13])[C:5]([F:11])=[CH:6][C:7]=1[N+:8]([O-])=O>C(O)C.[Pd]>[NH2:1][C:2]1[CH:3]=[C:4]([C:12]([F:15])([F:13])[F:14])[C:5]([F:11])=[CH:6][C:7]=1[NH2:8]

Participants

4

Reactant 1

HCID 27376865-Amino-2-fluoro-4-nitrobenzotrifluoride

Product 1

HCID 27744604-Fluoro-5-(trifluoromethyl)benzene-1,2-diamineYield 95.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-amino-6-fluoro-4-nitrobenzotrifluoride (328 mg, 1.45 mmol) and 10% Pd/C (50 mg) in ethanol (15 mL) was hydrogenated for 2 h at 25° C. under 25 psi H2. The catalyst was removed by filtration with celite and the solvent was removed by rota-evaporation to give 270 mg of 3,4-diamino-6-fluorobenzotrifluoride (95%) as a brown solid. 1H NMR (CDCl3): δ 3.432 (br, 4H), 6.469 (d, 1H, J=8.4 Hz); 6.860 (d, 1H, J=6.6 Hz).

Workup

  1. customThe catalyst was removed by filtration with celite
  2. customthe solvent was removed by rota-evaporation

Sources & evidence

ORD record
ord-84e5d9e1f92041698224dc1c5ffdf1c3
Source dataset
uspto-grants-1997_04
Patent number
US05620979

Reaction notes

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