Acetic Acid → 2-Amino-4,6-dimethylbenzoic acid

HRID 591779

Reaction equation

HRID 591779 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]([CH3:11])[CH:8]=[C:7]2[C:3]=1[C:4](=[O:13])C(=O)[NH:6]2.OO.Cl.C(O)(=[O:19])C>[OH-].[Na+]>[NH2:6][C:7]1[CH:8]=[C:9]([CH3:11])[CH:10]=[C:2]([CH3:1])[C:3]=1[C:4]([OH:13])=[O:19]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 23861614,6-dimethyl-1H-indole-2,3-dione

Product 1

HCID 133806232-Amino-4,6-dimethylbenzoic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

To a heated (70° C. bath temperature) deep red solution of 4,6-dimethyl-1H-indole-2,3-dione (1.00 g, 5.71 mmol) in 33% aqueous sodium hydroxide (35 mL) was added 35% hydrogen peroxide (3.33 g, 34.3 mmol) over a period of 5 minutes. The reaction mixture was heated for another 15 min, then cooled to room temperature, and ice was added. The pH was adjusted to approximately 8 with concentrated HCl at 0° C. and acidified further to pH approximately 6 with glacial acetic acid. The solid precipitated was filtered, washed well with cold water, and dried under vacuum at 40° C. overnight to obtain 2-amino-4,6-dimethyl-benzoic acid as a pale brown solid. Yield: 0.35 g (37%).

Workup

  1. temperatureThe reaction mixture was heated for another 15 min
  2. additionice was added
  3. customThe solid precipitated
  4. filtrationwas filtered
  5. washwashed well with cold water
  6. customdried under vacuum at 40° C. overnight

Sources & evidence

ORD record
ord-a507092f3d674698885eda1e829ff638
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Linked notes

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