Sodium Hydroxide → 4-(2-Methyl-1H-indol-3-yl)butanoic acid

HRID 1974560Notes

Reaction equation

HRID 1974560 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH2:11][CH2:12][CH2:13][C:14]([O:16]C)=[O:15])=[CH:8][CH:7]=[CH:6][CH:5]=2.[OH-].[Na+]>CO>[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10609557Methyl 4-(2-methylindol-3-yl)butyrate

Product 1

HCID 150472604-(2-Methyl-1H-indol-3-yl)butanoic acidYield 79.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of methyl 4-(2-methylindol-3-yl)-butyrate (1.65 g) in methanol (50 ml) was added 1N aqueous sodium hydroxide (18 ml) at 20° C. and the mixture was stirred at 20° C. for 3 hours. After evaporation of the solvent, the residue was poured into a mixture of ethyl acetate and 1N hydrochloric acid. The organic layer was separated, washed with water and brine, and dried over magnesium sulfate. After evaporation of solvent, the crystalline residue was washed with hexane to give 4(2-methylindol-3-yl)butyric acid (1.23 g) as reddish brown crystals.

Workup

  1. customAfter evaporation of the solvent
  2. additionthe residue was poured into a mixture of ethyl acetate and 1N hydrochloric acid
  3. customThe organic layer was separated
  4. washwashed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customAfter evaporation of solvent
  7. washthe crystalline residue was washed with hexane

Sources & evidence

ORD record
ord-01a2cf39deea47b2a9d5f4fa99c3a8cf
Source dataset
uspto-grants-1994_02
Patent number
US05283251

Reaction notes

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