1,3-Diethyl 2-oxopropanedioate → HCID 67532786, compound

HRID 1942139Notes

Reaction equation

HRID 1942139 reaction equation
[NH2:1][C:2]1[C:3]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.O=[C:18]([C:24](OCC)=[O:25])[C:19]([O:21][CH2:22][CH3:23])=[O:20]>C(O)C>[CH3:16][O:15][C:12]1[CH:13]=[CH:14][C:9]([N:8]2[C:24](=[O:25])[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[N:1][C:2]3[CH:7]=[CH:6][CH:5]=[N:4][C:3]2=3)=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 691051,3-Diethyl 2-oxopropanedioateHCID 11447232N~2~-(4-Methoxyphenyl)pyridine-2,3-diamine

Product 1

HCID 67532786HCID 67532786, compoundYield 37.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5.2 g (24 mmol) of 3-amino-2-(4-methoxyphenyl)aminopyridine was dissolved in ethanol (150 mL), and 4.6 g (27 mmol) of diethyl ketomalonate was added thereto. The mixture was heated to reflux for 9 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 purified by column chromatography (developing solvent:ethyl acetate:hexane=1:2), to obtain 2.9 g (yield: 37%) of ethyl 4-(4-methoxyphenyl)-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine-2-carboxylate as yellow crystals.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 9 hours
  3. customthe completion of the reaction
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue thus obtained
  6. customwas purified by column chromatography (developing solvent:ethyl acetate:hexane=1:2)

Sources & evidence

ORD record
ord-2657273f56934825ba127ae2c8c5e58a
Source dataset
uspto-grants-2013_03
Patent number
US08389523B2

Reaction notes

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