Pyridine → HCID 68473258, compound

HRID 1942141Notes

Reaction equation

HRID 1942141 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-c553e94efb9649449eaf78ce1c2d376b
Source dataset
uspto-grants-2013_03
Patent number
US08389523B2

Reaction notes

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