Sodium Iodide → 5-Chloro-1-(3-iodopropyl)indole-3-carboxaldehyde

HRID 2303949Notes

Reaction equation

HRID 2303949 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH2:12][CH2:13]Cl)[CH:6]=[C:5]2[CH:15]=[O:16].[I-:17].[Na+]>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH2:12][CH2:13][I:17])[CH:6]=[C:5]2[CH:15]=[O:16]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 184620915-Chloro-1-(3-chloropropyl)indole-3-carboxaldehyde

Product 1

HCID 184621165-Chloro-1-(3-iodopropyl)indole-3-carboxaldehydeYield 96%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A stirred solution of 5-chloro-1-(3-chloropropyl)indole-3-carboxaldehyde (3.8 g, 15 mmol) and sodium iodide (4.5 g, 30 mmol) in acetonitrile (50 mL) under argon was heated under reflux for 18 h, cooled to room temperature and partitioned between ether (3×30 mL) and water (50 mL). The combined organic extracts were washed (aqueous sodium metabisulfite solution, water, brine), dried (sodium sulfate) and concentrated in vacuo to give the product as a yellow oil (5.0 g, 96%) which was used immediately.

Workup

  1. temperatureunder reflux for 18 h
  2. custompartitioned between ether (3×30 mL) and water (50 mL)
  3. washThe combined organic extracts were washed (aqueous sodium metabisulfite solution, water, brine)
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0e7782ec23d24cd682978a095c17b783
Source dataset
uspto-grants-2002_08
Patent number
US06433175B1

Reaction notes

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