Methyl iodide → HCID 19030836, compound

HRID 266825Notes

Reaction equation

HRID 266825 reaction equation
[CH3:1][O:2][C:3]1[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[CH:25][C:4]=1[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:18][CH2:17][C:15]2=[O:16])=[CH:10][CH:9]=1)=[O:6].[H-].[Na+].[CH3:33]I>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[CH:25][C:4]=1[C:5]([N:7]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:18][CH2:17][C:15]2=[O:16])=[CH:10][CH:9]=1)[CH3:33])=[O:6]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 19030758HCID 19030758, compound

Product 1

HCID 19030836HCID 19030836, compoundYield 35.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 1-[4-(2,4-dimethoxybenzoylamino)phenyl]-3,4-dihydrocarbostyril (0.19 g) in dimethylformamide (8 ml) is added with stirring 60% sodium hydride (0.02 g) under ice cooling. The mixture is stirred at room temperature for 0.5 hour and thereto is added a solution of methyl iodide (0.08 g) in dimethylformamide (6 ml). The mixture is stirred at room temperature for 3 hours. The solvent is distilled off under reduced pressure and water is added to the residue. The mixture is extracted with dichloromethane, washed with water and dried with magnesium sulfate. The solvent is distilled off under reduced pressure and the resulting residue is purified by silica gel column chromatography to give 1-{4-[N-(2,4-dimethoxybenzoyl)-N-methylamino]phenyl}-3,4-dihydrocarbostyril (70 mg).

Workup

  1. stirringThe mixture is stirred at room temperature for 3 hours
  2. distillationThe solvent is distilled off under reduced pressure and water
  3. additionis added to the residue
  4. extractionThe mixture is extracted with dichloromethane
  5. washwashed with water
  6. dry with materialdried with magnesium sulfate
  7. distillationThe solvent is distilled off under reduced pressure
  8. customthe resulting residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a0e766295875498c8549440456d09766
Source dataset
uspto-grants-1997_07
Patent number
US05652247

Reaction notes

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