Ethyl Bromide → 1-Ethyl-1H-indole-3-carbaldehyde

HRID 1884822Notes

Reaction equation

HRID 1884822 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]=[O:11])=[CH:2]1.[CH2:12](Br)[CH3:13].[H-].[Na+]>CN(C)C=O>[CH2:12]([N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]=[O:11])=[CH:2]1)[CH3:13]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 10256Indole-3-Carboxaldehyde2×HCID 24758Sodium hydride

Product 1

HCID 5990901-Ethyl-1H-indole-3-carbaldehydeYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-ethylindole-3-carboxaldehyde was prepared from alkylation reaction of indole-3-carboxaldehyde. Indole-3-carboxaldehyde (900 mg, 6.2 mmol) was dissolved in 5 ml dimethylformamide, ethyl bromide (918 μl, 12 mmol) and sodium hydride (282.8 mg, 12 mmol) were added to the reaction mixture. Solution was stirred and refluxed for three hours. The reaction mixture was then evaporated to dryness and washed with water. Pale brown crystals were obtained with 80% yield.

Workup

  1. temperaturerefluxed for three hours
  2. customThe reaction mixture was then evaporated to dryness
  3. washwashed with water
  4. customPale brown crystals were obtained with 80% yield

Sources & evidence

ORD record
ord-40882a553ceb4b4b93ed98acb4a6c827
Source dataset
uspto-grants-2004_07
Patent number
US06767909B2

Reaction notes

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