Sodium Hydroxide → 4-Methoxy-1H-indole-2-carboxylic acid

HRID 969588Notes

Reaction equation

HRID 969588 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[C:6]([C:12]([O:14]C)=[O:13])[NH:7]2.[OH-].[Na+]>>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH:5]=[C:6]([C:12]([OH:14])=[O:13])[NH:7]2

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 688172methyl 4-methoxy-1H-indole-2-carboxylate

Product 1

HCID 9072484-Methoxy-1H-indole-2-carboxylic acidYield 99.6%

Procedure

The carboxylate (3a) (4 g, 19.49 mmol, 1 eq) obtained in (2-1) was added to aqueous solution of sodium hydroxide (2M, 98 mL, 0.20 mmol, 10 eq). The suspension was stirred and heated until the reaction mixture was uniform, and then refluxed for 30 minutes with heating. The mixture solution was acidified, and the resulting precipitate was extracted three times with ethyl acetate (100 mL). The extracts were combined, washed with water, dried over magnesium sulfate, and concentrated to give white solid of the title compound (4a) (3.71 g, yield 99%).

Workup

  1. temperatureheated until the reaction mixture
  2. temperaturerefluxed for 30 minutes
  3. temperaturewith heating
  4. extractionthe resulting precipitate was extracted three times with ethyl acetate (100 mL)
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-08f289b7468f42b5a454d0d13e9d1a49
Source dataset
uspto-grants-2007_12
Patent number
US07307098B2

Reaction notes

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