Methyl iodide → Benz[cd]indol-2(1H)-one, 1-methyl-

HRID 276905Notes

Reaction equation

HRID 276905 reaction equation
[NH:1]1[C:9]2[C:4]3[C:5](=[CH:10][CH:11]=[CH:12][C:3]=3[C:2]1=[O:13])[CH:6]=[CH:7][CH:8]=2.[H-].[Na+].CI.[C:18](OCC)(=O)C>CN(C)C=O.O>[CH3:18][N:1]1[C:9]2[C:4]3[C:5](=[CH:10][CH:11]=[CH:12][C:3]=3[C:2]1=[O:13])[CH:6]=[CH:7][CH:8]=2

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 67222benz(cd)indol-2(1H)-one

Product 1

HCID 121175Benz[cd]indol-2(1H)-one, 1-methyl-

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Benz[cd]indole-2(1H)-one (5.1 g, 30 mmol) was dissolved in anhydrous N,N-dimethylformamide (100 ml). Thereto was added sodium hydride (60% content, 1.2 g, 30 mmol), and the resulting solution was stirred for 20 minutes in an ice bath. The reaction solution was mixed with methyl iodide (2.6 ml, 42 mmol) and again stirred at a room temperature for 1 hour. The reaction solution was mixed with ethyl acetate (300 ml) and water (200 ml), and the reaction product was extracted with ethyl acetate. The ethyl acetate layer was separated, washed with water and then dried with anhydrous sodium sulfate. By evaporating ethyl acetate under a reduced pressure, 4.7 g (26 mmol, 74% in yield) of the title compound was obtained as yellow crystals.

Workup

  1. stirringagain stirred at a room temperature for 1 hour
  2. extractionthe reaction product was extracted with ethyl acetate
  3. customThe ethyl acetate layer was separated
  4. washwashed with water
  5. dry with materialdried with anhydrous sodium sulfate
  6. customBy evaporating ethyl acetate

Sources & evidence

ORD record
ord-33e2ed34f1e1450dbb0cd6f36ec282a8
Source dataset
uspto-grants-2002_03
Patent number
US06355642B1

Reaction notes

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