Hydrogen Peroxide → 2-Amino-4-bromobenzoic acid

HRID 1775502Notes

Reaction equation

HRID 1775502 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](=[O:12])C(=O)[NH:8]2)=[CH:4][CH:3]=1.[OH:13]O>[OH-].[Na+]>[NH2:8][C:9]1[CH:10]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=1[C:6]([OH:12])=[O:13]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 957161H-Indole-2,3-dione, 6-bromo-

Product 1

HCID 886912-Amino-4-bromobenzoic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

To a solution of the 6-bromoindoline-2,3-dione (e.g., 6-bromo-7-fluoroindoline-2,3-dione, 1 equiv) in 1 N NaOH (0.14 M) was added H2O2 (1.8 M) dropwise and the resulting mixture was stirred at room temperature until the reaction was complete (approximately 2 hours). The mixture was filtered and the filtrate was acidified to pH 2 with hydrochloric acid. The precipitate that formed was filtered, washed with water, and concentrated to provide the 2-amino-4-bromobenzoic acid (e.g., 2-amino-4-bromo-3-fluorobenzoic acid).

Workup

  1. custom(approximately 2 hours)
  2. filtrationThe mixture was filtered
  3. customThe precipitate that formed
  4. filtrationwas filtered
  5. washwashed with water
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b1042179c3994677b5122711cc9551f5
Source dataset
uspto-grants-2016_02
Patent number
US09260452B2

Reaction notes

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