Hydrogen Peroxide → 2-Amino-5-chloro-3-methylbenzoic acid

HRID 854944Notes

Reaction equation

HRID 854944 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([CH3:11])[CH:10]=1)[NH:7]C(=O)[C:5]2=[O:13].[OH-].[K+].OO.C(OCC)(=[O:20])C>CO>[NH2:7][C:8]1[C:9]([CH3:11])=[CH:10][C:2]([Cl:1])=[CH:3][C:4]=1[C:5]([OH:13])=[O:20]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 8857Ethyl AcetateHCID 14797Potassium HydroxideHCID 3667105-Chloro-7-methylisatin

Product 1

HCID 116440442-Amino-5-chloro-3-methylbenzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The 5-chloro-7-methyl-1H-indole-2,3-dione (25.0 g, 0.13 mol), potassium hydroxide (8.4 g, 0.15 mmol) and 30% hydrogen peroxide (21.6 g, 0.18 mol) were mixed together in methanol (300 mL) at 0° C. for 2 h followed by 16 h at room temperature. The solution was poured into ethyl acetate (500 mL) and extracted with I N hydrochloric acid (3×200 mL) followed by brine (1×50 mL). The solution was dried over sodium sulfate and solvent removed at reduced pressure. The 2-amino-5-chloro-3-methylbenzoic acid (18.0 g, 0.10 mmol) was isolated as a yellow solid (75% yield). HRMS m/z 185.0238; calcd 185.0244.

Workup

  1. extractionextracted with I N hydrochloric acid (3×200 mL)
  2. dry with materialThe solution was dried over sodium sulfate and solvent
  3. customremoved at reduced pressure

Sources & evidence

ORD record
ord-6866e5a6de484416ab4982b43116b460
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

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