Sodium hydride → Benzyl 4-(3,3-dimethoxypropyl)-6-methoxy-3-oxo-3,4-dihydroquinoxalin-1(2H)-carboxylate

HRID 1847080Notes

Reaction equation

HRID 1847080 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[CH2:8][C:7](=[O:23])[NH:6]2.[Br-].[Li+].[H-].[Na+].[CH3:28][O:29][CH:30]([O:34][CH3:35])[CH2:31][CH2:32]Br>CN(C)C=O.C(OCC)(=O)C>[CH3:28][O:29][CH:30]([O:34][CH3:35])[CH2:31][CH2:32][N:6]1[C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]([C:13]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:14])[CH2:8][C:7]1=[O:23]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 82050Lithium BromideHCID 1189323-Bromopropionaldehyde dimethylacetalHCID 86725003Benzyl 6-methoxy-3-oxo-3,4-dihydroquinoxalin-1(2H)-carboxylate

Product 1

HCID 86725004Benzyl 4-(3,3-dimethoxypropyl)-6-methoxy-3-oxo-3,4-dihydroquinoxalin-1(2H)-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of benzyl 6-methoxy-3-oxo-3,4-dihydroquinoxalin-1(2H)-carboxylate (291 mg, 0.932 mmol) in N,N-dimethylformamide (5 ml), lithium bromide (89 mg, 1.025 mmol) and subsequently sodium hydride (55%, 45 mg, 1.025 mmol) were added under a nitrogen gas atmosphere in an ice bath. The solution was stirred at room temperature for 1 hour. The reaction solution was cooled on ice again and 3-bromopropionaldehyde dimethyl acetal (0.184 ml, 1.212 mmol) was added thereto. After stirring overnight at room temperature, the reaction solution was diluted with ethyl acetate and washed sequentially with a saturated sodium hydrogen carbonate aqueous solution and saturated sodium chloride solution. After drying the resultant over anhydrous sodium sulfate, the solvent was removed under reduced pressure and the obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate) to yield 386 mg (quantitative) of the title compound in the form of a yellowish brown oil.

Workup

  1. temperatureThe reaction solution was cooled on ice again
  2. stirringAfter stirring overnight at room temperature
  3. washwashed sequentially with a saturated sodium hydrogen carbonate aqueous solution and saturated sodium chloride solution
  4. dry with materialAfter drying the resultant over anhydrous sodium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-5696cae981334e949fa81e4edf3d14f6
Source dataset
uspto-grants-2015_02
Patent number
US08952010B2

Reaction notes

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