Hydrogen Peroxide → 2-Amino-5-(propan-2-yl)benzoic acid

HRID 362916Notes

Reaction equation

HRID 362916 reaction equation
[OH:1]O.[CH:3]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11]C(=O)[C:9]2=[O:16])([CH3:5])[CH3:4].[OH-].[Na+]>O>[CH:3]([C:6]1[CH:7]=[C:8]([C:9]([OH:16])=[O:1])[C:12]([NH2:11])=[CH:13][CH:14]=1)([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 5898025-(propan-2-yl)-1H-indole-2,3-dione

Product 1

HCID 125621272-Amino-5-(propan-2-yl)benzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Step 1): 30% H2O2 (6 ml) was added to a solution of 5-isopropyl-1H-indole-2,3-dione [J. Med. Chem., 19, 391(1976)] (4.0 g, 21.1 mmol) in 1N-NaOH (15 ml) at 5° C. The mixture was stirred for 3 hours at room temperature and then poured into H2O and acidified. The precipitates were filtered to give 5-isopropylanthranilic acid, 2.6 g (68.6%): mp 93°-95° C.

Workup

  1. filtrationThe precipitates were filtered

Sources & evidence

ORD record
ord-72cdcd4d4e1f40869e1139e550392c5a
Source dataset
uspto-grants-1999_02
Patent number
US05872115

Reaction notes

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