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

HRID 2301103Notes

Reaction equation

HRID 2301103 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

1H-Benz[cd]indol-2-one (5.1 g, 30 mmol) was dissolved in anhydrous N,N-dimethylformamide (100 ml), and the solution was mixed with sodium hydride (60%, 1.2 g, 30 mmol) and stirred in an ice bath for 20 minutes. The reaction solution was mixed with methyl iodide (2.6 ml, 42 μmmol) and again stirred at room temperature for 1 hour. Ethyl acetate and water were added to the reaction solution. The reaction product was extracted with ethyl acetate, washed with saturated brine and dried with anhydrous sodium sulfate, the solvent was removed by evaporation under a reduced pressure, and then the thus obtained material was separated and purified by a silica gel column chromatography to obtain 4.7 g (26 mmol, 74% in yield) of the title compound.

Workup

  1. stirringagain stirred at room temperature for 1 hour
  2. extractionThe reaction product was extracted with ethyl acetate
  3. washwashed with saturated brine
  4. dry with materialdried with anhydrous sodium sulfate
  5. customthe solvent was removed by evaporation under a reduced pressure
  6. customthe thus obtained material was separated
  7. custompurified by a silica gel column chromatography
  8. customto obtain

Sources & evidence

ORD record
ord-2d6a73fb9f664cd893fca3febedd24ae
Source dataset
uspto-grants-2002_12
Patent number
US06498251B1

Reaction notes

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