Acetic Acid → 2-Fluoro-5-nitroaniline

HRID 1030326Notes

Reaction equation

HRID 1030326 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[F:13])([O-])=O.C(O)C.C(O)(=O)C.[H][H]>[Fe].[Rh].O>[F:13][C:5]1[CH:6]=[CH:7][C:8]([N+:10]([O-:12])=[O:11])=[CH:9][C:4]=1[NH2:1]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 6264DinitrofluorobenzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 677852-Fluoro-5-nitroanilineYield 78.8%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 23948RhodiumCatalystHCID 962WaterSolvent

Procedure

In a 500 ml Parr hydrogenation reactor were placed 8.50 g (0.0457 mole) of 2,4-dinitrofluorobenzene, 1.0 g (0.018 mole) of powdered iron, 0.15 g of 5% rhodium on alumina, 100 ml of ethanol, 100 ml of acetic acid, and 5 ml of water. The reaction was stopped after 140 psi of hydrogen had been absorbed, and the reaction mixture was then filtered. The filtrate was concentrated under reduced pressure, and water was added to the residue. Filtration yielded 5.62 g of crude 2-fluoro-5-nitroaniline. Analysis of the nmr spectrum of the product showed it to be >90% pure 2-fluoro-5-nitroaniline.

Workup

  1. customhad been absorbed
  2. filtrationthe reaction mixture was then filtered
  3. concentrationThe filtrate was concentrated under reduced pressure, and water
  4. additionwas added to the residue
  5. filtrationFiltration

Sources & evidence

ORD record
ord-1f9f067576ce415882727126b7fd594a
Source dataset
uspto-grants-1992_04
Patent number
US05105012

Reaction notes

Loading…