Ethyl Bromide → HCID 19795531, compound

HRID 1460737Notes

Reaction equation

HRID 1460737 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([O:11][CH3:12])=[CH:8][CH:9]=2)[NH:4][CH:3]=1.[OH-].[K+].[CH2:15](Br)[CH3:16]>CS(C)=O>[CH2:15]([N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[CH:6]=2)[C:2]([CH3:1])=[CH:3]1)[CH3:16]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 14797Potassium HydroxideHCID 3266536-methoxy-3-methyl-1H-indole

Product 1

HCID 19795531HCID 19795531, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4.6 g of 3-methyl-6-methoxyindole [Chem. ber. 98, 1727 (1965)] are presented in 29 ml of dimethyl sulfoxide. 6.6 ml of 10n aqueous KOH are then added, and 3.25 g of ethyl bromide are added dropwise at 20° C. in the course of 30'. 1 hour later the reaction mixture is poured onto water and extracted with toluene. Chromatography over silica gel (hexane/ether 5:1) gives 3.9 g of 1-ethyl-3-methyl-6-methoxyindol in the form of an oil.

Workup

  1. addition1 hour later the reaction mixture is poured onto water
  2. extractionextracted with toluene

Sources & evidence

ORD record
ord-d876e6fbcd3f49899a1f0e724f9ee842
Source dataset
uspto-grants-1991_12
Patent number
US05071986

Reaction notes

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