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

HRID 1183140Notes

Reaction equation

HRID 1183140 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.[H-].[Na+].I[CH3:15].[Cl-].[NH4+]>CN(C=O)C.O>[CH3:15][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

7

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 333703Indole-4-carboxaldehyde

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1H-indole-4-carbaldehyde (0.252 g, 1.72 mmol) in 8 mL of DMF was added sodium hydride (0.046 g, 1.9 mmol). After 5 min, iodomethane (0.13 mL, 2.1 mmol) was added. After 30 min, the reaction was treated with saturated aqueous ammonium chloride, diluted with water, and extracted 2× with dichloromethane. The combined organic fractions were washed 3× with water, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified via silica gel chromatography, eluting with 0-40% ethyl acetate in hexanes to provide 1-methyl-1H-indole-4-carbaldehyde that gave a proton NMR spectra consistent with theory and a mass ion (ES+) of 161.2 for [M+H]+.

Workup

  1. waitAfter 30 min
  2. extractionextracted 2× with dichloromethane
  3. washThe combined organic fractions were washed 3× with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified via silica gel chromatography
  8. washeluting with 0-40% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-abad30fa7fd74ef481bccfe756c34048
Source dataset
uspto-grants-2014_03
Patent number
US08664234B2

Reaction notes

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