1,3-Diethyl 2-oxopropanedioate → HCID 178470162, compound

HRID 336349Notes

Reaction equation

HRID 336349 reaction equation
O=[C:2]([C:8]([O:10]CC)=O)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[NH2:13][C:14]1[CH:19]=[C:18]([F:20])[C:17]([F:21])=[CH:16][C:15]=1[NH2:22]>C(O)C>[F:20][C:18]1[CH:19]=[C:14]2[C:15](=[CH:16][C:17]=1[F:21])[N:22]=[C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:8]([OH:10])=[N:13]2

Participants

4

Reactant 2

HCID 691051,3-Diethyl 2-oxopropanedioateHCID 27367551,2-Diamino-4,5-difluorobenzene

Product 1

HCID 178470162HCID 178470162, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of diethyl ketomalonate (1.11 mL, 7.3 mmol) and 1,2-diamino-4,5-difluorobenzene (1.0 g, 6.9 mmol) in anhydrous ethanol (20 mL) was heated at reflux under nitrogen for 3 h. The solvent was removed under reduced pressure and the residue was purified by flash column chromatography on silica gel, eluting with ethyl acetate/methylene chloride (1:2), to provide ethyl 6,7-difluoro-3-hydroxyquinoxaline-2-carboxylate as a light yellow solid:

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for 3 h
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was purified by flash column chromatography on silica gel
  5. washeluting with ethyl acetate/methylene chloride (1:2)

Sources & evidence

ORD record
ord-eba1dbf6d22a4f468a33c0eff8ab4191
Source dataset
uspto-grants-2014_11
Patent number
US08889683B2

Reaction notes

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