Methyl iodide → ethyl 5,6-dihydro-9-methyl-6-methoxy-4H-pyrrolo [3,2,1-ij]quinoline-2-carboxylate

HRID 650072Notes

Reaction equation

HRID 650072 reaction equation
[CH3:1]I.[OH:3][CH:4]1[C:13]2[C:8]3=[C:9]([CH:15]=[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[N:7]3[CH2:6][CH2:5]1)[C:10]([CH3:14])=[CH:11][CH:12]=2.[H-].[Na+]>O1CCCC1>[CH3:14][C:10]1[C:9]2[CH:15]=[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[N:7]3[C:8]=2[C:13]([CH:4]([O:3][CH3:1])[CH2:5][CH2:6]3)=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 21714278ethyl 5,6-dihydro-6-hydroxy-9-methyl-4H-pyrrolo [3,2,1-ij]quinoline-2-carboxylate

Product 1

HCID 21714363ethyl 5,6-dihydro-9-methyl-6-methoxy-4H-pyrrolo [3,2,1-ij]quinoline-2-carboxylateYield 58.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl iodide (0.55 g, 3.86 mmol) was added dropwise to a mixture of ethyl 5,6-dihydro-6-hydroxy-9-methyl-4H-pyrrolo[3,2,1-ij]quinoline-2-carboxylate (0.50 g, 1.93 mmol), 60% sodium hydride (0.08 g, 1.93 mmol) and tetrahydrofuran (20 ml) with stirring at room temperature, and the resulting mixture was stirred at room temperature for another 2 hours. The reaction mixture was poured into ice water and extracted three times with ethyl acetate, and the extract solution was washed with a 5% aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: ethyl acetate/n-hexane=5/95) to obtain 0.31 g of ethyl 5,6-dihydro-9-methyl-6-methoxy-4H-pyrrolo[3,2,1-ij]quinoline-2-carboxylate.

Workup

  1. stirringthe resulting mixture was stirred at room temperature for another 2 hours
  2. extractionextracted three times with ethyl acetate
  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 resulting residue was purified by a silica gel column chromatography (eluent: ethyl acetate/n-hexane=5/95)

Sources & evidence

ORD record
ord-0e2cc7b16fd04783932f788897cf71be
Source dataset
uspto-grants-2001_08
Patent number
US06271251B1

Reaction notes

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