Hydrogen Peroxide → 2-Amino-3-chloro-4-methoxybenzoic acid

HRID 420072Notes

Reaction equation

HRID 420072 reaction equation
[Cl:1][C:2]1[C:3]([O:13][CH3:14])=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9]C(=O)[C:7]2=[O:12].[OH-:15].[Na+].[Na+].[Cl-].OO>O.C(Cl)Cl>[NH2:9][C:10]1[C:2]([Cl:1])=[C:3]([O:13][CH3:14])[CH:4]=[CH:5][C:6]=1[C:7]([OH:12])=[O:15]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 666505277-chloro-6-methoxy-1H-indole-2,3-dione

Product 1

HCID 666505632-Amino-3-chloro-4-methoxybenzoic acidYield 36%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A suspension of compound 103d (6.03 g, 28.52 mmol), NaOH (1.25 g, 31.37 mmol), and NaCl (3.49 g, 59.89 mmol) in water (60 mL) was stirred at room temperature for 30 min and was then ice-cooled. H2O2 was added dropwise. The mixture was stirred at 0° C. for 20 min and at room temperature for 3 hrs. The reaction mixture was quenched with glacial AcOH, filtered, and washed with water. The solid obtained was dissolved in DCM, dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude material was purified by chromatography on silica gel (DCM/MeOH) to yield compound 104d as an orange solid in 36% yield.

Workup

  1. temperatureice-cooled
  2. stirringThe mixture was stirred at 0° C. for 20 min and at room temperature for 3 hrs
  3. customThe reaction mixture was quenched with glacial AcOH
  4. filtrationfiltered
  5. washwashed with water
  6. customThe solid obtained
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe crude material was purified by chromatography on silica gel (DCM/MeOH)

Sources & evidence

ORD record
ord-8345de03bd9c4a5eb8da0115f0dbe628
Source dataset
uspto-grants-2012_01
Patent number
US08093379B2

Reaction notes

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