2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 5-Acetyl-7-(benzyloxy)quinolin-2(1H)-one

HRID 1372906Notes

Reaction equation

HRID 1372906 reaction equation
C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.[C:15]([C:18]1[CH:27]=[C:26]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:25]=[C:24]2[C:19]=1[CH2:20][CH2:21][C:22](=[O:36])[NH:23]2)(=[O:17])[CH3:16]>O1CCOCC1>[C:15]([C:18]1[CH:27]=[C:26]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:25]=[C:24]2[C:19]=1[CH:20]=[CH:21][C:22](=[O:36])[NH:23]2)(=[O:17])[CH3:16]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 210728505-acetyl-7-benzyloxy-3,4-dihydro-1H-quinolin-2-one

Product 1

HCID 210728495-Acetyl-7-(benzyloxy)quinolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

DDQ (15.0 g, 66.08 mmol) is added to a suspension of 5-acetyl-7-benzyloxy-3,4-dihydro-1H-quinolin-2-one (13.0 g, 44.02 mmol) in dioxane (130 mL) and the mixture is refluxed for 30 minutes. The reaction mixture is cooled to ambient temperature and stirred for a further 2 hours. The precipitate formed is filtered off, washed with dioxane (2×20 mL) and dissolved in dichloromethane/methanol (9:1, 600 mL). The organic phase is washed with sodium bicarbonate solution (2×100 mL), dried with sodium sulphate and evaporated down. The residue is stirred with methanol, the precipitate formed is filtered off and dried. Yield: 8.3 g (64%); mass spectroscopy: [M+H]+=294.

Workup

  1. temperaturethe mixture is refluxed for 30 minutes
  2. customThe precipitate formed
  3. filtrationis filtered off
  4. washwashed with dioxane (2×20 mL)
  5. dissolutiondissolved in dichloromethane/methanol (9:1, 600 mL)
  6. washThe organic phase is washed with sodium bicarbonate solution (2×100 mL)
  7. dry with materialdried with sodium sulphate
  8. customevaporated down
  9. stirringThe residue is stirred with methanol
  10. customthe precipitate formed
  11. filtrationis filtered off
  12. customdried

Sources & evidence

ORD record
ord-9abda30a1fb645c5b63dcc2b4d7f07ab
Source dataset
uspto-grants-2007_01
Patent number
US07160882B2

Reaction notes

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