1,3-Diethyl 2-oxopropanedioate → Ethyl 5-chloro-2-oxo-1,2-dihydroquinoxaline-3-carboxylate

HRID 1942151Notes

Reaction equation

HRID 1942151 reaction equation
[Cl:1][C:2]1[C:3]([NH2:9])=[C:4]([NH2:8])[CH:5]=[CH:6][CH:7]=1.O=[C:11]([C:17](OCC)=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[N:9]=[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:17](=[O:18])[NH:8]2

Participants

4

Reactant 2

HCID 691051,3-Diethyl 2-oxopropanedioateHCID 3462489(2-Amino-3-chlorophenyl)amine

Product 1

HCID 67531483Ethyl 5-chloro-2-oxo-1,2-dihydroquinoxaline-3-carboxylateYield 56.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

10.5 g (73.6 mmol) of 3-chloro-1,2-phenylenediamine and 12.8 g (73.5 mmol) of diethyl ketomalonate were dissolved in ethanol, and the solution was heated to reflux for 3 hours. While heating to reflux, ethanol was added thereto until precipitated crystals dissolved. The reaction mixture was cooled to room temperature, and then precipitated crystals were separated by filtration. The filter cake was washed with cold ethanol, and then dried, to obtain 10.5 g (yield: 51%) of ethyl 5-chloro-2-oxo-1,2-dihydroquinoxaline-3-carboxylate as pale yellow acicular crystals.

Workup

  1. temperaturethe solution was heated
  2. temperatureto reflux for 3 hours
  3. temperatureWhile heating
  4. temperatureto reflux
  5. customuntil precipitated crystals
  6. dissolutiondissolved
  7. customprecipitated crystals
  8. customwere separated by filtration
  9. washThe filter cake was washed with cold ethanol
  10. customdried

Sources & evidence

ORD record
ord-e4dd8dab326b47cd84951be91ddabc2e
Source dataset
uspto-grants-2013_03
Patent number
US08389523B2

Reaction notes

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