2-Chloro-4-fluoro-5-nitrobenzoic Acid → 5-Amino-2-chloro-4-fluorobenzoic acid

HRID 22635Notes

Reaction equation

HRID 22635 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([N+:12]([O-])=O)=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]>C(O)(=O)C.O.C(OCC)(=O)C.[Fe]>[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([NH2:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

6

Reactant 1

HCID 72108282-Chloro-4-fluoro-5-nitrobenzoic Acid

Product 1

HCID 120567845-Amino-2-chloro-4-fluorobenzoic acid

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-chloro-4-fluoro-5-nitrobenzoic acid (18.0 g, 0.0824 mol) in 75 ml of acetic acid was heated at reflux temperature. Iron powder (18.4 g, 0.328 mol) was added in several portions and the resulting suspension was cooled to room temperature and diluted with water and ethyl acetate. The mixture was filtered and the filtrate was saved. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to afford the title compound as a tan solid. Yield: 9.00 g (58.1%); mp.: 153-155° C.; identified by NMR and mass spectral analysis.

Workup

  1. temperatureat reflux temperature
  2. filtrationThe mixture was filtered
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1151058879a045ecbe8c8101f445d1c7
Source dataset
uspto-grants-2005_02
Patent number
US06849618B2

Reaction notes

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