Water → ethyl 1-(cyanomethyl)-1H-indole-2-carboxylate

HRID 963085Notes

Reaction equation

HRID 963085 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([O:12][CH2:13][CH3:14])=[O:11].[H-].[Na+].Br[CH2:18][C:19]#[N:20].O>CN(C)C=O>[C:19]([CH2:18][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([O:12][CH2:13][CH3:14])=[O:11])#[N:20]

Participants

6

Reactant 4

HCID 962WaterHCID 11534BromoacetonitrileHCID 24758Sodium hydrideHCID 73125Ethyl indole-2-carboxylate

Product 1

HCID 713238ethyl 1-(cyanomethyl)-1H-indole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl indole-2-carboxylate (6.0 g) was dissolved in dimethylformamide (60 ml) and sodium hydride (60% in oil, 1.4 g) was added under ice-cooling. After stirring for 30 minutes, bromoacetonitrile (2.3 ml) was added and the mixture was stirred. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated, and the residue was recrystallized from ethyl acetate to give 6.6 g of ethyl 1-cyanomethylindole-2-carboxylate.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-de556aba425542409ffe1fe5e0ba98e8
Source dataset
uspto-grants-1998_06
Patent number
US05760032

Reaction notes

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