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Lithium hydroxide, monohydrate → 3-Methoxyindole-6-carboxylic acid

HRID 23946
Notes
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Reaction equation

HRID 23946 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]([O:15]C)=[O:14])[CH:11]=2)[C:6]([O:17][CH3:18])=[CH:5]1)(=O)C.O.[OH-].[Li+]>C1COCC1.O>[CH3:18][O:17][C:6]1[C:7]2[C:12](=[CH:11][C:10]([C:13]([OH:15])=[O:14])=[CH:9][CH:8]=2)[NH:4][CH:5]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 22569986Methyl 1-acetyl-3-methoxyindole-6-carboxylate

Product 1

HCID 225701063-Methoxyindole-6-carboxylic acidYield 87.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl 1-acetyl-3-methoxyindole-6-carboxylate (74 mg, 0.3 mmol) in THF (10 ml) and water (2 ml) was added lithium hydroxide hydrate (63 mg, 1.5 mmol). The reaction mixture was warmed to 50° C. and stirred for 3 h. The THF was removed under reduced pressure and the pH of the aqueous phase adjusted to 3. Extraction of the aqueous layer with ethyl acetate, drying and concentration gave the acid (50 mg, 87%);

Workup

  1. customThe THF was removed under reduced pressure
  2. extractionExtraction of the aqueous layer with ethyl acetate
  3. customdrying
  4. concentrationconcentration

Sources & evidence

ORD record
ord-a114a88948d74f7f916aad27722aebe7
Source dataset
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06855715B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes