Hydrochloric Acid → HCID 68993151, compound

HRID 749185Notes

Reaction equation

HRID 749185 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[C:8]2[C:4]=1[C:5](=[O:15])C(=O)[NH:7]2.[OH:16]O.[ClH:18]>[OH-].[Na+]>[ClH:18].[NH2:7][C:8]1[CH:9]=[C:10]([O:12][CH3:13])[CH:11]=[C:3]([O:2][CH3:1])[C:4]=1[C:5]([OH:15])=[O:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 115575224,6-dimethoxy-2,3-dihydro-1H-indole-2,3-dione

Product 1

HCID 68993151HCID 68993151, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
75 °C

Procedure

4,6-Dimethoxyisatin (5.00 g, 24.0 mmol) was dissolved in 33% (w/v) aqueous sodium hydroxide solution (42 ml) at 75° C. To this solution was added hydrogen peroxide (30%, 8 ml) dropwise over 30 minutes. The reaction was stirred for an hour at 75° C. and then cooled to room temperature. Ice was added, and the reaction mixture acidified to pH 1 with concentrated hydrochloric acid. The resulting precipitate was filtered, washed with water and dried in vacuo to yield 2-amino-4,6-dimethoxybenzoic acid hydrochloride salt (3.3 g, 59% yield) acid as a pale yellow solid:

Workup

  1. temperaturecooled to room temperature
  2. additionIce was added
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-d37a2eacef214e259aedee0937c24c7f
Source dataset
uspto-grants-2008_07
Patent number
US07402585B2

Reaction notes

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