Sodium Iodide → 1-[2-(1,3-Dioxolan-2-yl)ethyl]-7-methoxy-4-methylquinolin-2(1H)one

HRID 1847094Notes

Reaction equation

HRID 1847094 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([CH3:14])=[CH:8][C:9](=[O:13])[NH:10]2)=[CH:5][CH:4]=1.[I-].[Na+].[H-].[Li+].Br[CH2:20][CH2:21][CH:22]1[O:26][CH2:25][CH2:24][O:23]1>CN(C)C=O>[O:23]1[CH2:24][CH2:25][O:26][CH:22]1[CH2:21][CH2:20][N:10]1[C:11]2[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:12]=2)[C:7]([CH3:14])=[CH:8][C:9]1=[O:13]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 62714Lithium hydrideHCID 877762-(2-Bromoethyl)-1,3-dioxolaneHCID 7615487-Methoxy-4-methylquinolin-2-ol

Product 1

HCID 867250161-[2-(1,3-Dioxolan-2-yl)ethyl]-7-methoxy-4-methylquinolin-2(1H)oneYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In N,N-dimethylformamide (15 ml) was dissolved 7-methoxy-4-methylquinolin-2(1H)one (1.5 g, 6.06 mmol), sodium iodide (2.3 g, 15.9 mmol) was added thereto under cooling on ice and lithium hydride (188 mg, 15.9 mmol) was gradually added thereto. After stirring for 1 hour under cooling on ice, 2-(2-bromoethyl)-1,3-dioxolane (1.6 ml, 15.9 mmol) was gradually added thereto. The reaction solution was stirred overnight at room temperature and then the extract was partitioned into ethyl acetate-water, whereby the organic layer was separated. The obtained organic layer was washed with water and saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to yield 1 g (57%) of the title compound.

Workup

  1. additionwas added
  2. additionwas gradually added
  3. additionwas gradually added
  4. stirringThe reaction solution was stirred overnight at room temperature
  5. customthe extract was partitioned into ethyl acetate-water, whereby the organic layer
  6. customwas separated
  7. washThe obtained organic layer was washed with water and saturated sodium chloride solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe solvent was removed under reduced pressure
  10. customthe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-46ad198c99d248efa1850f817df162cf
Source dataset
uspto-grants-2015_02
Patent number
US08952010B2

Reaction notes

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