Indole → 1H-Indole-1-acetonitrile

HRID 1072614Notes

Reaction equation

HRID 1072614 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].Br[CH2:13][C:14]#[N:15]>CN(C)C=O.C(OCC)(=O)C>[N:1]1([CH2:13][C:14]#[N:15])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

6

Reactant 3

HCID 798IndoleHCID 11534BromoacetonitrileHCID 24758Sodium hydride

Product 1

HCID 122309041H-Indole-1-acetonitrileYield 27.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 0° C. solution of indole (7 g, 59.8 mmol) in 200 ml of dimethylformamide is treated with NaH (60% dispersion in mineral oil; 3.1 g, 77.7 mmol). After 20 minutes, bromoacetonitrile (4.2 ml, 59.8 mmol) is added, and the resulting mixture is allowed to slowly warm to ambient temperature and stir overnight. The reaction mixture is diluted with ethyl acetate (500 ml) and washed with H2O (3×200 ml). The organic layer is dried over Na2SO4 and concentrated in vacuo. The crude residue is purified by flash chromatography (SiO2; 5% then 20% ethyl acetate in hexanes) to give 2.53 g of indol-1-yl-acetonitrile (27%).

Workup

  1. washwashed with H2O (3×200 ml)
  2. dry with materialThe organic layer is dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe crude residue is purified by flash chromatography (SiO2

Sources & evidence

ORD record
ord-1bd3b4102d7041c39f77b46820cdcbb8
Source dataset
uspto-grants-2005_06
Patent number
US06911463B2

Reaction notes

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