Methyl iodide → 1-Methyl-1H-indole-4-carbaldehyde

HRID 1533988Notes

Reaction equation

HRID 1533988 reaction equation
[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([CH:10]=[O:11])[C:4]=2[CH:3]=[CH:2]1.[CH2:12]([N+](CCCC)(CCCC)CCCC)CCC.CI>C(Cl)Cl.[OH-].[Na+]>[CH3:12][N:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([CH:10]=[O:11])[C:4]=2[CH:3]=[CH:2]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 16028TetrabutylammoniumHCID 333703Indole-4-carboxaldehyde

Product 1

HCID 172211111-Methyl-1H-indole-4-carbaldehydeYield 98.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

34 g of indol 4-carboxaldehyde in 800 ml of methylen chloride were mixed for 4 hours at ambient temperature with 79.5 g of tetrabutyl ammonium hydrogeno sulfate and 16.04 ml of methyl iodide in 400 ml of 5N sodium hydroxide and 300 ml of methylene chloride were added, followed by decanting and extraction was effected with methylene chloride. The organic phase was washed with a saturated aqueous solution of sodium chloride, dried and concentrated to dryness. The residue was chromatographed on silica (eluant: methylene chloride) to obtain 36.8 g of the expected product melting at <40° C.

Workup

  1. additionwere added
  2. customby decanting
  3. extractionextraction
  4. washThe organic phase was washed with a saturated aqueous solution of sodium chloride
  5. customdried
  6. concentrationconcentrated to dryness
  7. customThe residue was chromatographed on silica (eluant: methylene chloride)

Sources & evidence

ORD record
ord-a0bf3477e1e84e6d8dfe7a2203c14563
Source dataset
uspto-grants-1992_02
Patent number
US05086070

Reaction notes

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