Potassium Hydroxide → 5,6,7-Trimethoxy-1H-indole-2-carboxylic acid

HRID 720328

Reaction equation

HRID 720328 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[C:10]([O:14][CH3:15])[C:11]=1[O:12][CH3:13])[NH:8][C:7]([C:16]([O:18]C)=[O:17])=[CH:6]2.[OH-].[K+]>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[C:10]([O:14][CH3:15])[C:11]=1[O:12][CH3:13])[NH:8][C:7]([C:16]([OH:18])=[O:17])=[CH:6]2

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 4453649methyl 5,6,7-trimethoxy-1H-indole-2-carboxylate

Product 1

HCID 8210525,6,7-Trimethoxy-1H-indole-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 5,6,7-trimethoxyindole-2-carboxylate (700 mg) was dissolved in methanol (13 mL), potassium hydroxide powder (450 mg) was added to the solution, and the mixture was stirred for 3 hours under reflux. After allowing the reaction mixture to cool, it was concentrated under reduced pressure, and water was added to the residue. The resultant water layer was washed with ether and then neutralized with diluted hydrochloric acid. Crystals deposited were collected by filtration and dried to obtain the title compound.

Workup

  1. temperatureunder reflux
  2. temperatureto cool
  3. concentrationit was concentrated under reduced pressure, and water
  4. additionwas added to the residue
  5. washThe resultant water layer was washed with ether
  6. filtrationCrystals deposited were collected by filtration
  7. customdried

Sources & evidence

ORD record
ord-ef47eda3e0f746f9ab94ee01fb7f597b
Source dataset
uspto-grants-2006_11
Patent number
US07135473B2

Linked notes

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