Water → 2-Methylindol-4-yloxyacetic Acid Methyl Ester

HRID 351642

Reaction equation

HRID 351642 reaction equation
C[C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[C:8]([OH:11])[CH:7]=[CH:6][CH:5]=2.[C:12](=O)([O-])[O-].[K+].[K+].Br[CH2:19][C:20]([O:22][CH3:23])=[O:21].O>CN(C)C=O>[CH3:23][O:22][C:20](=[O:21])[CH:19]([O:11][C:8]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:9]=1[CH:10]=[CH:2][NH:3]2)[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 5902254-Hydroxy-2-methylindole

Product 1

HCID 691303762-Methylindol-4-yloxyacetic Acid Methyl Ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 2-methyl-4-hydroxyindole (5 g) in N,N-dimethylformamide (50 ml) was added anhydrous potassium carbonate 11.7 g) and methyl bromoacetate (3.54 ml) at room temperature, and the mixture was stirred at 80° C. for 2 hours. To the reaction solution was added iced water to give the title compound (5.4 g) having the following physical data.

Sources & evidence

ORD record
ord-ddab40e05b894d31ab8c82b4ed422700
Source dataset
uspto-grants-2004_06
Patent number
US06743793B2

Linked notes

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