2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 21252869, compound

HRID 1530992Notes

Reaction equation

HRID 1530992 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6]4=[C:7]([C:17](=[O:20])[CH2:18][CH2:19][N:5]4[C:4]=2[CH:3]=1)[CH:8]=[C:9]([O:15][CH3:16])[CH:10]=3.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.[OH-].[Na+]>O1CCOCC1>[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6]4=[C:7]([C:17](=[O:20])[CH:18]=[CH:19][N:5]4[C:4]=2[CH:3]=1)[CH:8]=[C:9]([O:15][CH3:16])[CH:10]=3

Participants

5

Reactant 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 14798Sodium HydroxideHCID 9905551HCID 9905551, compound

Product 1

HCID 21252869HCID 21252869, compoundYield 70.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

9-bromo-5,6-dihydro-2-methoxy-4H-pyrido[3,2,1-jk]carbazole-4-one (1.0 g) obtained in Example 101, step 6 was dissolved in anhydrous dioxane (40 ml), and DDQ (1.45 g) was added at room temperature. The mixture was heated under reflux in an argon atmosphere for 3 hours and allowed to cool. The reaction mixture was added to 1N aqueous solution of sodium hydroxide (150 ml), and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting crude crystals were washed with ethanol and recovered by filtration to obtain the title compound (0.7 g, 70%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux in an argon atmosphere for 3 hours
  3. temperatureto cool
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. washThe resulting crude crystals were washed with ethanol
  9. filtrationrecovered by filtration

Sources & evidence

ORD record
ord-a7af3cdf407b45f68cf1bbdb69753798
Source dataset
uspto-grants-2001_03
Patent number
US06197768B1

Reaction notes

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