1,3-Diethyl 2-oxopropanedioate → HCID 68476438, compound

HRID 240339Notes

Reaction equation

HRID 240339 reaction equation
[NH2:1][C:2]1[C:3]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.O=[C:16]([C:22](OCC)=[O:23])[C:17]([O:19][CH2:20][CH3:21])=[O:18]>C(O)C>[O:23]=[C:22]1[N:8]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:3]2[N:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=[C:16]1[C:17]([O:19][CH2:20][CH3:21])=[O:18]

Participants

4

Reactant 2

HCID 691051,3-Diethyl 2-oxopropanedioateHCID 106790912-N-phenylpyridine-2,3-diamine

Product 1

HCID 68476438HCID 68476438, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

11.68 g (63 mmol) of 3-amino-2-anilinopyridine was dissolved in ethanol (150 mL), and 12.07 g (69 mmol) of diethyl ketomalonate was added thereto. The mixture was heated to reflux for 4 hours while stirring. After confirming the completion of the reaction, the reaction solution was cooled to room temperature, and the solvent was distilled off under reduced pressure. The residue thus obtained was washed using diisopropyl ether, to obtain 10.74 g (yield: 58%) of ethyl 3-oxo-4-phenyl-3,4-dihydropyrido[2,3-b]pyrazine-2-carboxylate as pale yellow crystals.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 4 hours
  3. customthe completion of the reaction
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue thus obtained
  6. washwas washed

Sources & evidence

ORD record
ord-c3f84edb831348a89ae03de8728ec866
Source dataset
uspto-grants-2014_02
Patent number
US08648075B2

Reaction notes

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