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

HRID 2395742Notes

Reaction equation

HRID 2395742 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-028c4db8e8614fac8891008e711f015f
Source dataset
uspto-grants-1996_02
Patent number
US05489593

Reaction notes

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