Pyridine → HCID 68473258, compound

HRID 240344Notes

Reaction equation

HRID 240344 reaction equation
[O:1]=[C:2]1[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.[CH3:17][O:18][C:19]1[CH:20]=[C:21](OB(O)O)[CH:22]=[CH:23][CH:24]=1.N1C=CC=CC=1>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:17][O:18][C:19]1[CH:24]=[C:23]([N:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[N:10]=[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:2]2=[O:1])[CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 248643Ethyl 3-hydroxyquinoxaline-2-carboxylateHCID 221738233-Methoxyphenylboric acid

Product 1

HCID 68473258HCID 68473258, compoundYield 205.6%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

2.0 g (9.2 mmol) of ethyl 2-oxo-1,2-dihydroquinoxaline-3-carboxylate was dissolved in dichloromethane (100 mL), and 2.8 g (1.8 mmol) of 3-methoxyphenylboric acid, 3.3 g (1.8 mmol) of anhydrous copper (II) acetate and 1.4 g (1.8 mmol) of pyridine were added thereto. The mixture was stirred for 72 hours at room temperature. After completion of the reaction, the inorganic matter was separated by filtration, and then the solvent was distilled off under reduced pressure. The residue thus obtained was purified by column chromatography (developing solvent: ethyl acetate:hexane=1:1), to obtain 1.2 g (yield: 42%) of ethyl 1-(3-methoxyphenyl)-2-oxo-1,2-dihydroquinoxaline-3-carboxylate as a white powder.

Workup

  1. customAfter completion of the reaction
  2. customthe inorganic matter was separated by filtration
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue thus obtained
  5. customwas purified by column chromatography (developing solvent: ethyl acetate:hexane=1:1)

Sources & evidence

ORD record
ord-1f294f7e544442849824d645ebf8287f
Source dataset
uspto-grants-2014_02
Patent number
US08648075B2

Reaction notes

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