Hydrochloric Acid → 2-Amino-4,6-dimethoxybenzoic acid

HRID 130324Notes

Reaction equation

HRID 130324 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].[Na+].OO.Cl>C(O)(=O)C>[CH3:13][O:12][C:10]1[CH:9]=[C:8]([NH2:7])[C:4](=[C:3]([O:2][CH3:1])[CH:11]=1)[C:5]([OH:15])=[O:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 784Hydrogen Peroxide2×HCID 14798Sodium HydroxideHCID 115575224,6-dimethoxy-2,3-dihydro-1H-indole-2,3-dione

Product 1

HCID 116584562-Amino-4,6-dimethoxybenzoic acidYield 50%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a heated mixture (in an oversized flask) of 13 g (63 mmol) 4,6-dimethoxyindole-2,3-dione prepared in Example 1 and 108 ml of 33% NaOH solution was carefully added 20 ml of a 30% solution of H2O2. A vigorous exothermic reaction occurs. After all H2O2 was added, the reaction mixture was maintained at 100° C. for an additional 10 min. The pH of the solution was brought to 8 with concentrated HCl and acidified to pH 5-6 with acetic acid. The solid was filtered, washed with water and dried to yield 6.2 g of 4,6-dimethoxyanthranilic acid as a pale brown solid (50% yield).

Workup

  1. customA vigorous exothermic reaction
  2. filtrationThe solid was filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-20bbbca9340448099b93274c4af3fd17
Source dataset
uspto-grants-2008_06
Patent number
US07381730B2

Reaction notes

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