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

HRID 22635Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 22635
[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]

Komponenten

6

Edukt 1

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 23925IronKatalysatorHCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-1151058879a045ecbe8c8101f445d1c7
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06849618B2

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