Hydrogen Peroxide → 2-Amino-5-methoxy-4-methylbenzoic acid

HRID 1157443Notes

Reaction equation

HRID 1157443 reaction equation
OO.[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][C:13]=1[CH3:14])[NH:10]C(=O)[C:8]2=[O:16].S(=O)(=O)(O)[OH:18]>[OH-].[Na+]>[NH2:10][C:11]1[CH:12]=[C:13]([CH3:14])[C:5]([O:4][CH3:3])=[CH:6][C:7]=1[C:8]([OH:16])=[O:18]

Participants

5

Reactant 3

HCID 784Hydrogen Peroxide2×HCID 1118Sulfuric AcidHCID 543291845-Methoxy-6-methylindoline-2,3-dione

Product 1

HCID 212914972-Amino-5-methoxy-4-methylbenzoic acidYield 61%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

10% Hydrogen peroxide (H2O2) (80 mL) was added dropwise to a stirring solution of 5-methoxy-6-methyl-1H-indole-2,3-dione (4.7 g, 24.6 mmol) in 3N NaOH (aq.) (100 mL). The H2O2 solution was added over a period of 1.5 h in order to keep the temperature below 35° C. The solution was then acidified to pH 4 with 2.5M sulfuric acid. A precipitate formed and was collected by filtration. The solid was washed with water and dried to give 2-amino-5-methoxy-4-methylbenzoic acid (2.7 g, 14.9 mmol, 61%).

Workup

  1. customthe temperature below 35° C
  2. customA precipitate formed
  3. filtrationwas collected by filtration
  4. washThe solid was washed with water
  5. customdried

Sources & evidence

ORD record
ord-ab690afa79244967aa07c56e8fe07704
Source dataset
uspto-grants-2010_10
Patent number
US07807686B2

Reaction notes

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