Sodium Iodide → 1-(3,3-Dimethoxypropyl)-7-methoxyquinoxalin-2(1H)-one

HRID 1846996Notes

Reaction equation

HRID 1846996 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([N:7]=[CH:8][C:9](=[O:13])[NH:10]2)=[CH:5][CH:4]=1.[H-].[Li+].Br[CH2:17][CH2:18][CH:19]([O:22][CH3:23])[O:20][CH3:21].[I-].[Na+]>CN(C)C=O.C(OCC)(=O)C>[CH3:21][O:20][CH:19]([O:22][CH3:23])[CH2:18][CH2:17][N:10]1[C:11]2[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:12]=2)[N:7]=[CH:8][C:9]1=[O:13]

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 62714Lithium hydrideHCID 1189323-Bromopropionaldehyde dimethylacetalHCID 4913197-Methoxy-1,2-dihydroquinoxalin-2-one

Product 1

HCID 867249271-(3,3-Dimethoxypropyl)-7-methoxyquinoxalin-2(1H)-oneYield 72%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

7-Methoxyquinoxalin-2(1H)-one (synthesized with reference to WO2009/1126; 4.13 g, 23.4 mmol) was dissolved in N,N-dimethylformamide (103 ml). The solution was cooled in an ice bath, lithium hydride (purity 90%, 248 mg, 28.1 mmol) was then added thereto and the mixture was stirred at room temperature for 40 minutes. The reaction solution was cooled in an ice bath again, 3-bromo-1,1-dimethoxypropane (3.78 ml, 28.1 mmol) and sodium iodide (4.21 g, 28.1 mmol) were added and then the mixture was stirred at room temperature for 2 days. The reaction solution was diluted with ethyl acetate, washed sequentially with saturated sodium chloride solution (×2), water and saturated sodium chloride solution, dried over magnesium sulfate and the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate) to yield 4.68 g (72%) of the title compound in the form of a yellow syrup.

Workup

  1. temperatureThe solution was cooled in an ice bath
  2. temperatureThe reaction solution was cooled in an ice bath again
  3. stirringthe mixture was stirred at room temperature for 2 days
  4. washwashed sequentially with saturated sodium chloride solution (×2), water and saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-9ad34cbd113e4d54b35af0aa459d6b5f
Source dataset
uspto-grants-2015_02
Patent number
US08952010B2

Reaction notes

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