Sodium Iodide → 5-Methoxy-1-(4-iodobutyl)indole-3-carboxaldehyde

HRID 2303957Notes

Reaction equation

HRID 2303957 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][CH2:13][CH2:14][CH2:15]Cl)[CH:7]=[C:6]2[CH:17]=[O:18].[I-:19].[Na+]>C(#N)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][CH2:13][CH2:14][CH2:15][I:19])[CH:7]=[C:6]2[CH:17]=[O:18]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 184620835-Methoxy-1-(4-chlorobutyl)indole-3-carboxaldehyde

Product 1

HCID 184620695-Methoxy-1-(4-iodobutyl)indole-3-carboxaldehyde

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A stirred solution of 5-methoxy-1-(4-chlorobutyl)indole-3-carboxaldehyde and sodium iodide in acetonitrile under argon is heated under reflux for 18 h, cooled to room temperature and partitioned between ether and water. The combined organic extracts are washed (aqueous sodium metabisulfite solution, water, brine), dried (sodium sulfate) and concentrated in vacuo to give the product.

Workup

  1. temperatureunder reflux for 18 h
  2. custompartitioned between ether and water
  3. washThe combined organic extracts are washed (aqueous sodium metabisulfite solution, water, brine)
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated in vacuo
  6. customto give the product

Sources & evidence

ORD record
ord-98b5809d616445678b0704544d83cb45
Source dataset
uspto-grants-2002_08
Patent number
US06433175B1

Reaction notes

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