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

HRID 1403294Notes

Reaction equation

HRID 1403294 reaction equation
C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.[O:15]=[C:16]1[NH:25][C:24]2[C:19](=[CH:20][CH:21]=[C:22]([C:26]([O:28][CH3:29])=[O:27])[CH:23]=2)[NH:18][CH:17]1[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>O1CCOCC1>[O:15]=[C:16]1[NH:25][C:24]2[C:19](=[CH:20][CH:21]=[C:22]([C:26]([O:28][CH3:29])=[O:27])[CH:23]=2)[N:18]=[C:17]1[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=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

DDQ (21.25 g, 93.6 mmol, 2.62 equiv) was added to a stirred solution of methyl 3-oxo-2-phenyl-1,2,3,4-tetrahydroquinoxaline-6-carboxylate (10.07 g, 35.7 mmol, 1.00 equiv) in dioxane (750 mL) and allowed to react, with stirring, overnight at room temperature. The solids were collected by filtration. The filter cake was washed with 2×500 mL of aqueous K2CO3 (saturated). This resulted in 7.29 g (crude) of methyl 3-oxo-2-phenyl-3,4-dihydroquinoxaline-6-carboxylate as an off-white solid. LC-MS (ES, m/z): 281 [M+H]+.

Workup

  1. customto react
  2. filtrationThe solids were collected by filtration
  3. washThe filter cake was washed with 2×500 mL of aqueous K2CO3 (saturated)
  4. customThis resulted in 7.29 g (crude) of methyl 3-oxo-2-phenyl-3,4-dihydroquinoxaline-6-carboxylate as an off-white solid

Sources & evidence

ORD record
ord-09b2a8e92dda4f67ba021027fa82c1df
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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