Ammonium Chloride → 2-Amino-4-bromobenzoic acid

HRID 1270403Notes

Reaction equation

HRID 1270403 reaction equation
[Cl-].[NH4+].[Br:3][C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=[O:9])=[C:6]([N+:13]([O-])=O)[CH:5]=1>C(O)C.O.[Fe]>[NH2:13][C:6]1[CH:5]=[C:4]([Br:3])[CH:12]=[CH:11][C:7]=1[C:8]([OH:10])=[O:9]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 37744674-Bromo-2-nitrobenzoic acid

Product 1

HCID 886912-Amino-4-bromobenzoic acid

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Iron powder (4.15 g, 74.38 mmol) and ammonium chloride (3.32 g, 62.0 mmol) were added to a solution of 4-bromo-2-nitrobenzoic acid [J. Am. Chem. Soc. 1952, 74, 5621] (3.05 g, 12.4 mmol) in ethanol (50 mL) and water (25 mL) and the mixture was heated at reflux. After 6 h, the reaction was filtered, washed with ethanol, and concentrated in vacuo. The crude material was dissolved in water (150 mL) and concentrated HCl (30 mL) and stirred at ambient temperature for 16 h. The mixture was extracted with ethyl acetate (2×200 mL) and the organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure to give the title compound. MS: m/z=216 (M+1).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux
  3. filtrationthe reaction was filtered
  4. washwashed with ethanol
  5. concentrationconcentrated in vacuo
  6. dissolutionThe crude material was dissolved in water (150 mL)
  7. extractionThe mixture was extracted with ethyl acetate (2×200 mL)
  8. dry with materialthe organic layer was dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-caef88d8f7fa45cf928845e142ad6370
Source dataset
uspto-grants-2007_04
Patent number
US07202251B2

Reaction notes

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