Potassium Hydroxide → 5-Methoxy-1-(4-chlorobutyl)indole-3-carboxaldehyde

HRID 2303956Notes

Reaction equation

HRID 2303956 reaction equation
[OH-].[K+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]=[C:8]2[CH:14]=[O:15].Br[CH2:17][CH2:18][CH2:19][CH2:20][Cl:21]>CS(C)=O>[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH2:17][CH2:18][CH2:19][CH2:20][Cl:21])[CH:9]=[C:8]2[CH:14]=[O:15]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 813641-Bromo-4-chlorobutaneHCID 827585-Methoxyindole-3-carbaldehyde

Product 1

HCID 184620835-Methoxy-1-(4-chlorobutyl)indole-3-carboxaldehyde

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a stirred mixture of powdered potassium hydroxide in methyl sulfoxide is added dropwise a solution of 5-methoxyindole-3-carboxaldehyde in methyl sulfoxide. The mixture is stirred for 30 min and 1-bromo-4-chlorobutane is added dropwise. The mixture is stirred for 1 h and partitioned between ethyl acetate and water. The combined organic extracts are washed (water, brine), dried (sodium sulfate) and concentrated in vacuo to give the product.

Workup

  1. stirringThe mixture is stirred for 1 h
  2. custompartitioned between ethyl acetate and water
  3. washThe combined organic extracts are washed (water, brine)
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated in vacuo
  6. customto give the product

Sources & evidence

ORD record
ord-fce0826d3e3b4940a105ed50b9445d2f
Source dataset
uspto-grants-2002_08
Patent number
US06433175B1

Reaction notes

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