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

HRID 1405262Notes

Reaction equation

HRID 1405262 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 stifling, 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. customovernight
  3. customat room temperature
  4. filtrationThe solids were collected by filtration
  5. washThe filter cake was washed with 2×500 mL of aqueous K2CO3 (saturated)
  6. 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-41d9c4fc11eb486e8312b03adc7300fa
Source dataset
uspto-grants-2014_12
Patent number
US08916561B2

Reaction notes

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