Dimethyl(methylene)ammounium iodide → HCID 22139377, compound

HRID 1825752Notes

Reaction equation

HRID 1825752 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[CH:10]=[O:11])[CH:3]=[CH:2]1.[CH3:12][N+:13]([CH3:15])=[CH2:14].[I-]>C(#N)C>[CH3:12][N:13]([CH2:15][C:3]1[C:4]2[C:9](=[C:8]([CH:10]=[O:11])[CH:7]=[CH:6][CH:5]=2)[NH:1][CH:2]=1)[CH3:14]

Participants

4

Reactant 2

HCID 2724133Dimethyl(methylene)ammounium iodideHCID 2734629Indole-7-carboxaldehyde

Product 1

HCID 22139377HCID 22139377, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 7-indolcarboxaldehyde (0.25 g, 1.7 mmol) and Eschenmoser's salt (0.35 g, 1.9 mmol) in dry acetonitrile (10 ml) was heated under reflux for 2½h. After cooling, solvent was removed under reduced pressure and water was added to the residue. The cooled mixture (ice bath) was made alkaline with 10% sodium hydroxide and then extracted with dichloromethane. The combined organic extracts were washed with brine, dried over anhydrous magnesium sulfate and evaporated to afford 0.25 g (74%) of the entitled product.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2½h
  3. temperatureAfter cooling
  4. customsolvent was removed under reduced pressure and water
  5. additionwas added to the residue
  6. extractionextracted with dichloromethane
  7. washThe combined organic extracts were washed with brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customevaporated

Sources & evidence

ORD record
ord-767edd0e6e864825a054d59a361077c5
Source dataset
uspto-grants-2006_05
Patent number
US07049312B1

Reaction notes

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