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

HRID 33381Notes

Reaction equation

HRID 33381 reaction equation
[C:1]([C:4]1[CH:13]=[C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:11]=[C:10]2[C:5]=1[CH2:6][CH2:7][C:8](=[O:22])[NH:9]2)(=[O:3])[CH3:2].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCOCC1>[C:1]([C:4]1[CH:13]=[C:12]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:11]=[C:10]2[C:5]=1[CH:6]=[CH:7][C:8](=[O:22])[NH:9]2)(=[O:3])[CH3:2]

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

13.0 g (44 mmol) 5-acetyl-7-benzyloxy-3,4-dihydro-1H-quinolin-2-one are suspended in 130 mL dioxane and combined with 15.0 g (66 mmol) of 2,3-dichloro-5,6-dicyanobenzoquinone. The mixture is refluxed for 30 minutes, cooled to ambient temperature and stirred for a further 2 hours. The solid is filtered off, washed with dioxane and dissolved in 600 mL dichloromethane/methanol (9:1). The solution is washed with sodium hydrogen carbonate solution, dried with sodium sulphate and evaporated down. Then the residue is suspended in methanol, filtered and dried.

Workup

  1. temperatureThe mixture is refluxed for 30 minutes
  2. filtrationThe solid is filtered off
  3. washwashed with dioxane
  4. dissolutiondissolved in 600 mL dichloromethane/methanol (9:1)
  5. washThe solution is washed with sodium hydrogen carbonate solution
  6. dry with materialdried with sodium sulphate
  7. customevaporated down
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-77418d8c43974fee8734f31649c38fcb
Source dataset
uspto-grants-2008_09
Patent number
US07429583B2

Reaction notes

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