Dimethylformamide → HCID 117660479, compound

HRID 1428387Notes

Reaction equation

HRID 1428387 reaction equation
[H-].[Na+].CN(C=O)C.[Cl:8][C:9]1[CH:18]=[C:17]2[C:12]([N:13]=[CH:14][C:15](=[O:19])[NH:16]2)=[CH:11][CH:10]=1.Br[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]>O>[Cl:8][C:9]1[CH:18]=[C:17]2[C:12]([N:13]=[CH:14][C:15](=[O:19])[N:16]2[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 4913187-Chloro-2-quinoxalinone

Product 1

HCID 117660479HCID 117660479, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under a nitrogen gas flow, to a mixture of NaH (55% in oil, 515 mg) and DMF (5 mL) was added a mixture of 7-chloroquinoxalin-2(1H)-one (2.00 g) and DMF (35 mL) under ice-cooling, followed by stirring at room temperature for 30 minutes. The reaction mixture was ice-cooled and ethyl bromoacetate (1.3 mL) was added thereto, followed by stirring at room temperature for 7 hours. The reaction mixture was added to water, followed by extraction with EtOAc. The organic layer was washed with water and brine in this order, dried over Na2SO4, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform/MeOH=100/0-98/2). The obtained solid was washed with Hex to obtain ethyl (7-chloro-2-oxoquinoxalin-1(2H)-yl)acetate (2.21 g).

Workup

  1. additionwas added
  2. temperaturecooling
  3. temperaturecooled
  4. stirringby stirring at room temperature for 7 hours
  5. extractionfollowed by extraction with EtOAc
  6. washThe organic layer was washed with water and brine in this order
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (eluent: chloroform/MeOH=100/0-98/2)
  10. washThe obtained solid was washed with Hex

Sources & evidence

ORD record
ord-1ef841f99a3f44678824fd150534f425
Source dataset
uspto-grants-2015_01
Patent number
US08937087B2

Reaction notes

Loading…