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

HRID 255316Notes

Reaction equation

HRID 255316 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH2:10])[C:5]([NH2:9])=[CH:6][C:7]=1[F:8].[O:11]=[CH:12][C:13](OCC)=O>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:11])[CH:13]=[N:10]2

Participants

4

Reactant 2

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

Product 1

HCID 63243396,7-Difluoro-1,2-dihydroquinoxalin-2-oneYield 73%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 4,5-difluorobenzene-1,2-diamine (4.7 g, 32.6 mmol) in ethanol (75 mL) was added ethyl oxoacetate (50 wt % in toluene, 13.3 mL, 65.3 mmol). The reaction was stirred at room temperature overnight. The resulting precipitate was collected by filtration, washed with ethanol, and dried under reduced pressure to give 4.3 g (73%) of the product as a colorless solid.

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed with ethanol
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-4efe318e23c0456692c5b9710d64e7aa
Source dataset
uspto-grants-2011_01
Patent number
US07875715B2

Reaction notes

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