Ethyl oxoacetate → 6,7-Difluoro-1,2-dihydroquinoxalin-2-one

HRID 656980Notes

Reaction equation

HRID 656980 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH2:10])[C:5]([NH2:9])=[CH:6][C:7]=1[F:8].[C:11](OCC)(=O)[CH:12]=[O:13]>C1(C)C=CC=CC=1.C(O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][C:7]=1[F:8])[NH:9][C:12](=[O:13])[CH:11]=[N:10]2

Participants

5

Reactant 2

HCID 70211Ethyl oxoacetateHCID 27367551,2-Diamino-4,5-difluorobenzene

Product 1

HCID 63243396,7-Difluoro-1,2-dihydroquinoxalin-2-one

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

A mixture of 4,5-difluoro-1,2-benzenediamine (0.60 g) and 50% ethyl glyoxalate in toluene (0.87 ml) in ethanol (25 ml) was heated under reflux for 2 hours then cooled. After refrigeration overnight, the resulting solid was collected and washed with ice-cold ethanol and dried under vacuum to give a solid (0.57 g; 75%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. temperaturethen cooled
  4. customthe resulting solid was collected
  5. washwashed with ice-cold ethanol
  6. customdried under vacuum
  7. customto give a solid (0.57 g; 75%)

Sources & evidence

ORD record
ord-7606aba2855d46779e36807cb9f09725
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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