Acetic Acid → 2-Fluoro-5-nitroaniline

HRID 1030324Notes

Reaction equation

HRID 1030324 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]>[Pd].[Fe].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 85.6%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

To a 500 ml Parr hydrogenation reactor were charged 8.1 g (0.0438 mole) of 2,4-dinitrofluorobenzene, 0.5 g of 5% palladium on carbon catalyst, 1.0 g (0.018 mole) of powdered iron, 150 ml of ethanol, 50 ml of glacial acetic acid, and 5 ml of water. The reaction was stopped after 152 psi of hydrogen had been absorbed. The reaction mixture was filtered, and the filtrate was evaporated under reduced pressure leaving a red solid. This solid was passed through a pad of silica gel, eluting with methylene chloride. The solvent was evaporated from the eluate, producing 5.85 g of crude 2-fluoro-5-nitroaniline, m.p. 94°-96° C. Analysis of the nmr spectrum of this material showed it to be >90% pure 2-fluoro-5-nitroaniline.

Workup

  1. customhad been absorbed
  2. filtrationThe reaction mixture was filtered
  3. customthe filtrate was evaporated under reduced pressure
  4. customleaving a red solid
  5. washeluting with methylene chloride
  6. customThe solvent was evaporated from the eluate,

Sources & evidence

ORD record
ord-7a0829fa43484d1390b72a71d88c4593
Source dataset
uspto-grants-1992_04
Patent number
US05105012

Reaction notes

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