Water → 6-methoxy-1H-indole-2-carboxylic acid

HRID 864410

Reaction equation

HRID 864410 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[C:8]([C:12]([O:14]C)=[O:13])[NH:9]2)=[CH:5][CH:4]=1.O.[OH-].[K+]>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[C:8]([C:12]([OH:14])=[O:13])[NH:9]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 688173Methyl-6-methoxy-2-indolecarboxylate

Product 1

HCID 4103276-methoxy-1H-indole-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Methyl 6-methoxyindole-2-carboxylate (PREPARATION 62, 571 g) is dissolved in 70 ml of dioxane and 7 ml of water and 1.87 g of crushed potassium hydroxide are added. The reaction is heated to 50° and stirred 1.5 hr. The reaction mixture is acidified to pH 4-5 and extracted several times with methanol/chloroform (10/90). The organic layers are combined and dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give the title acid, NMR (300 MHz, d4-CD3OD) 7.47, 7.08, 6.90, 6.72 and 3.82 δ.

Workup

  1. temperatureThe reaction is heated to 50°
  2. extractionextracted several times with methanol/chloroform (10/90)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-aee4b0b90d2d4da99c0cbecb2c07a819
Source dataset
uspto-grants-1996_10
Patent number
US05563142

Linked notes

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