Hydrochloric Acid → 2-Amino-5-bromo-3-nitrobenzoic acid

HRID 1470598Notes

Reaction equation

HRID 1470598 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([N+:11]([O-:13])=[O:12])[CH:10]=1)[NH:7]C(=O)[C:5]2=[O:15].[OH:16]O.Cl>[OH-].[Na+]>[NH2:7][C:8]1[C:9]([N+:11]([O-:13])=[O:12])=[CH:10][C:2]([Br:1])=[CH:3][C:4]=1[C:5]([OH:15])=[O:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 12624101HCID 12624101, compound

Product 1

HCID 184314782-Amino-5-bromo-3-nitrobenzoic acidYield 94.5%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

To a slurry of 5-bromo-7-nitro-1H-indole-2,3-dione (5.5 g, 20.3 mmol) in aqueous 5N NaOH solution (23.2 mL) was added an aq. solution of 33% hydrogen peroxide solution (4.96 mL) slowly at 0° C. After completion of the addition, the reaction mixture was stirred at room temperature for 4 h. After completion of the reaction, the reaction mixture was acidified with 2N HCl and the solid the resulting precipitate was filtered, washed with water (2-3 times) and dried under vacuum to obtain the title compound as yellow solid (5 g, 94.5%).

Workup

  1. additionAfter completion of the addition
  2. customAfter completion of the reaction
  3. filtrationthe solid the resulting precipitate was filtered
  4. washwashed with water (2-3 times)
  5. customdried under vacuum

Sources & evidence

ORD record
ord-13b2ff8756be4d42935bd3446aca9bf2
Source dataset
uspto-grants-2015_04
Patent number
US09006454B2

Reaction notes

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