Methyl iodide → 7-((2,2-Dimethyl-[1,3]dioxolan-4-yl)methyl)-6-methoxy-1-methyl-1,2,3,4-tetrahydroquinolin-2-one

HRID 494988Notes

Reaction equation

HRID 494988 reaction equation
[CH3:1][C:2]1([CH3:21])[O:6][CH:5]([CH2:7][C:8]2[CH:17]=[C:16]3[C:11]([CH2:12][CH2:13][C:14](=[O:18])[NH:15]3)=[CH:10][C:9]=2[O:19][CH3:20])[CH2:4][O:3]1.[H-].[Na+].I[CH3:25]>CN(C)C=O.C(OCC)(=O)C>[CH3:1][C:2]1([CH3:21])[O:6][CH:5]([CH2:7][C:8]2[CH:17]=[C:16]3[C:11]([CH2:12][CH2:13][C:14](=[O:18])[N:15]3[CH3:25])=[CH:10][C:9]=2[O:19][CH3:20])[CH2:4][O:3]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 576827707-((2,2-Dimethyl-[1,3]dioxolan-4-yl)methyl)-6-methoxy-1,2,3,4-tetrahydroquinolin-2-one

Product 1

HCID 576828007-((2,2-Dimethyl-[1,3]dioxolan-4-yl)methyl)-6-methoxy-1-methyl-1,2,3,4-tetrahydroquinolin-2-oneYield 98.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

300 mg of 7-((2,2-dimethyl-[1,3]dioxolan-4-yl)methyl)-6-methoxy-1,2,3,4-tetrahydroquinolin-2-one was dissolved in 6 ml of N,N-dimethylformamide. While cooling on ice, 49 mg of 60% sodium hydride was added to the reaction solution, and the obtained mixture was then stirred at room temperature for 30 minutes. Thereafter, 0.29 g of iodomethane was added to the reaction solution while cooling on ice. The obtained mixture was stirred at room temperature for 2 hours. The reaction solution was diluted with ethyl acetate and then washed with a saturated ammonium chloride aqueous solution and a saturated sodium chloride aqueous solution. The organic layer was dried over magnesium sulfate and then concentrated under a reduced pressure. The residue was purified by NH silica gel column chromatography (hexane-ethyl acetate), so as to obtain 310 mg of the subject compound.

Workup

  1. additionwas added to the reaction solution
  2. temperaturewhile cooling on ice
  3. stirringThe obtained mixture was stirred at room temperature for 2 hours
  4. washwashed with a saturated ammonium chloride aqueous solution
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated under a reduced pressure
  7. customThe residue was purified by NH silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-3105d4fdfffc4d4cbf78324f688b8a3b
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

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