Dimethylformamide → HCID 15461773, compound

HRID 2269732Notes

Reaction equation

HRID 2269732 reaction equation
[H-].[Na+].CN(C=O)C.[O:8]=[C:9]1[NH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=[C:10]1[C:19]([O:21][CH2:22][CH3:23])=[O:20].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O>[CH2:24]([N:18]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=[C:10]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:9]1=[O:8])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 248643Ethyl 3-hydroxyquinoxaline-2-carboxylate

Product 1

HCID 15461773HCID 15461773, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydride (60% dispersion in oil; 0.8 g) was added to a DMF (20 ml) solution of ethyl 3,4-dihydro-3-oxo-2-quinoxalinecarboxylate (4.4 g) under ice-cooling. The reaction mixture was stirred for 10 minutes, to which was added benzyl bromide (2.4 g). The reaction mixture was stirred at room temperature for 3 hours, poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, then dried and concentrated. The residue was recrystallized from ethyl acetate-hexane to obtain the entitled compound (3.6 g).

Workup

  1. temperaturecooling
  2. stirringThe reaction mixture was stirred at room temperature for 3 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-e55dd937de244508b81126ce88d76a9a
Source dataset
uspto-grants-2001_12
Patent number
US06329389B1

Reaction notes

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