Acetic Acid → 2-Fluoro-5-nitroaniline

HRID 1030325Notes

Reaction equation

HRID 1030325 reaction equation
C(O)(=O)C.O.[N+:6]([C:9]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[CH:12]=[CH:11][C:10]=1[F:18])([O-])=O.[H][H]>[Pt]=O.[Fe].C(O)C>[F:18][C:10]1[CH:11]=[CH:12][C:13]([N+:15]([O-:17])=[O:16])=[CH:14][C:9]=1[NH2:6]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 6264DinitrofluorobenzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 677852-Fluoro-5-nitroanilineYield 89.3%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

To a mixture of 40 ml of glacial acetic acid, 5 ml of water, and 8.32 g (0.0447 mole) of 2,4-dinitrofluorobenzene were added 0.10 g (0.00044 mole) of platinum oxide and 0.50 g (0.0090 mole) of powdered iron. Subsequently, 160 ml of ethanol was added to this mixture, and the entire reaction mixture was placed in a 500 ml Parr hydrogenation reactor. The reaction was stopped after 144 psi of hydrogen had been absorbed, and the reaction mixture was then filtered. The filtrate was evaporated under reduced pressure, and the residue was passed through a pad of silica gel, eluting with methylene chloride. The solvent was evaporated from the eluate under reduced pressure, producing 6.23 g of crude 2-fluoro-5-nitroaniline, m.p. 90°-92° C. Analysis of the nmr spectrum of this material showed it to be at least 85% pure 2-fluoro-5-nitroaniline.

Workup

  1. customthe entire reaction mixture
  2. customhad been absorbed
  3. filtrationthe reaction mixture was then filtered
  4. customThe filtrate was evaporated under reduced pressure
  5. washeluting with methylene chloride
  6. customThe solvent was evaporated from the eluate under reduced pressure

Sources & evidence

ORD record
ord-8a012645ff07458f9f7ebd7b2ea11cf3
Source dataset
uspto-grants-1992_04
Patent number
US05105012

Reaction notes

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