Acetic Acid → 5-Methoxy-4,6,7-trimethylindole-2-carboxylic acid

HRID 864388Notes

Reaction equation

HRID 864388 reaction equation
[CH3:1][O:2][C:3]1(C)[CH:11]=[C:10]([CH3:12])[C:9]2[C:5]([CH:6]=[C:7]([C:13]([O:15]CC)=[O:14])[N:8]=2)=[C:4]1[CH3:18].[OH-].[K+].[C:22](O)(=O)C>C(O)C>[CH3:1][O:2][C:3]1[C:4]([CH3:18])=[C:5]2[C:9](=[C:10]([CH3:12])[C:11]=1[CH3:22])[NH:8][C:7]([C:13]([OH:15])=[O:14])=[CH:6]2

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14797Potassium HydroxideHCID 19418845Ethyl 5-methoxy-4,5,7-trimethylindole-2-carboxylate

Product 1

HCID 194187895-Methoxy-4,6,7-trimethylindole-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 5-methoxy-4,5,7 trimethylindole-2-carboxylate (PREPARATION 19, 1.04 g) in ethanol (30 ml) containing potassium hydroxide (45%, 2.5 ml) is heated under reflux for 1.5 hr. The mixture is acidified with acetic acid (2 ml) and concentrated under reduced pressure. The residue is mixed with water (200 ml) and filtered. The filter cake is washed with water and dried to give the title compound.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 1.5 hr
  3. concentrationconcentrated under reduced pressure
  4. additionThe residue is mixed with water (200 ml)
  5. filtrationfiltered
  6. washThe filter cake is washed with water
  7. customdried

Sources & evidence

ORD record
ord-21f20374ba0d45d1805b48c1b1caccea
Source dataset
uspto-grants-1996_10
Patent number
US05563142

Reaction notes

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