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

HRID 1646948Notes

Reaction equation

HRID 1646948 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.[CH3:12]I>C(Cl)Cl.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.[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 2

HCID 6328Methyl iodideHCID 333703Indole-4-carboxaldehyde

Product 1

HCID 172211111-Methyl-1H-indole-4-carbaldehyde

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6344DichloromethaneSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

34 g of indol 4-carboxaldehyde in 800 ml of methylene chloride were mixed for 4 hours at ambient temperature with 79.5 g of tetrabutyl ammonium hydrogen 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. Tho 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. customTho residue was chromatographed on silica (eluant: methylene chloride)

Sources & evidence

ORD record
ord-5961bcb3bdb545d7b19e4cd78071c3b7
Source dataset
uspto-grants-1993_01
Patent number
US05182282

Reaction notes

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