Methyl iodide → HCID 10999231, compound

HRID 2395357Notes

Reaction equation

HRID 2395357 reaction equation
[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]3[CH2:10][CH2:11][CH2:12][C:3]([C:4]=23)=[C:2]1[C:13]([O:15][CH2:16][CH3:17])=[O:14].[H-].[Na+].[CH3:20]I>CN(C)C=O>[CH3:20][N:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]3[CH2:10][CH2:11][CH2:12][C:3]([C:4]=23)=[C:2]1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 18972171HCID 18972171, compound

Product 1

HCID 10999231HCID 10999231, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl 1,3,4,5-tetrahydro-benz[cd]indole-2-carboxylate (1.00 g , 4.36 mmol) in N,N-dimethylformamide (20 ml) was added 60% sodium hydride (0.19 g, 4.80 mmol), followed by stirring at room temperature for 30 minutes. Then, methyl iodide (1.86 g, 13.1 mmol) was added and the resulting mixture was stirred at room temperature for 2 hours, after which the reaction mixture was poured into ice water, followed by extraction with ethyl acetate (twice). The extract solution was washed with a 5% aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by a silica gel column chromatography (eluent: ethyl acetate/n-hexane=1.5/98.5) to obtain ethyl 1,3,4,5-tetrahydro-1-methyl-benz[cd]indole-2-carboxylate (1.03 g).

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 2 hours
  2. extractionfollowed by extraction with ethyl acetate (twice)
  3. washThe extract solution was washed with a 5% aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by a silica gel column chromatography (eluent: ethyl acetate/n-hexane=1.5/98.5)

Sources & evidence

ORD record
ord-b747187023c74b6e93fa1b42e77b01b6
Source dataset
uspto-grants-1998_09
Patent number
US05814654

Reaction notes

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