2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → Methyl 3-oxo-2-phenyl-3,4-dihydroquinoxaline-6-carboxylate

HRID 2205098Notes

Reaction equation

HRID 2205098 reaction equation
[O:1]=[C:2]1[NH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:12]([O:14][CH3:15])=[O:13])[CH:9]=2)[NH:4][CH:3]1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>O1CCOCC1>[O:1]=[C:2]1[NH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:12]([O:14][CH3:15])=[O:13])[CH:9]=2)[N:4]=[C:3]1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 67042084Methyl 3-oxo-2-phenyl-1,2,3,4-tetrahydroquinoxaline-6-carboxylate

Product 1

HCID 67041704Methyl 3-oxo-2-phenyl-3,4-dihydroquinoxaline-6-carboxylate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of methyl 3-oxo-2-phenyl-1,2,3,4-tetrahydroquinoxaline-6-carboxylate (400 mg, 0.57 mmol, 1.00 equiv, 40%) in dioxane (30 mL) and DDQ (340 mg, 1.50 mmol, 2.64 equiv) was allowed to react, with stirring, for 3 hrs at room temperature in a 50-mL round-bottom flask. The solids were collected by filtration and discarded. The resulting mixture was washed with 1×20 mL of saturated K2CO3, and the organic layer was concentrated in vacuo to result in 10 mg (6%) of methyl 3-oxo-2-phenyl-3,4-dihydroquinoxaline-6-carboxylate as a yellow solid.

Workup

  1. customto react
  2. filtrationThe solids were collected by filtration
  3. washThe resulting mixture was washed with 1×20 mL of saturated K2CO3
  4. concentrationthe organic layer was concentrated in vacuo
  5. customto result in 10 mg (6%) of methyl 3-oxo-2-phenyl-3,4-dihydroquinoxaline-6-carboxylate as a yellow solid

Sources & evidence

ORD record
ord-e1e775b705e646a49b3f744baff4d559
Source dataset
uspto-grants-2016_06
Patent number
US09370522B2

Reaction notes

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