4-Bromo-2-nitrobenzoic acid → 2-Amino-4-bromobenzoic acid

HRID 1725897Notes

Reaction equation

HRID 1725897 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([N+:11]([O-])=O)[CH:3]=1>[OH-].[NH4+].O.S([O-])([O-])(=O)=O.[Fe+2].[NH4+]>[NH2:11][C:4]1[CH:3]=[C:2]([Br:1])[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7]

Participants

5

Reactant 1

HCID 37744674-Bromo-2-nitrobenzoic acid

Product 1

HCID 886912-Amino-4-bromobenzoic acid

Reagents, catalysts & solvents 3

HCID 21900404ammonium iron (II) sulfateCatalystHCID 962WaterSolventHCID 14923Ammonium HydroxideSolvent

Procedure

A mixture of Example 125A (5.1 g, 20.7 mmol) in concentrated ammonium hydroxide (102 mL) was treated with a solution of ammonium iron (II) sulfate (49 g, 125.1 mmol) in water (102 mL) over 5 minutes, heated to reflux for 2 minutes, cooled to room temperature, filtered through diatomaceous earth (Celite®), acidified to pH 1 with concentrated HCl, and extracted with ethyl acetate. The organic layer was dried (Na2SO4), filtered, and concentrated to provide the desired product. MS (ESI(−)) m/e 214, 216 (M−H)−, 1H NMR (300 MHz, DMSO-d6) δ 7.59 (d, 1H), 6.97 (d, 1H), 6.63 (dd, 1H), 3.32 (br s, 3H).

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 minutes
  3. filtrationfiltered through diatomaceous earth (Celite®)
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f9f47c851557475180f5023237d6c346
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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