2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 10-bromo-2-methoxy-4H-pyrido[3,2,1-jk]carbazole-4-one

HRID 1530970Notes

Reaction equation

HRID 1530970 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]3[CH2:19][CH2:18][C:17](=[O:20])[C:8]4[CH:9]=[C:10]([O:15][CH3:16])[CH:11]=[C:12]([C:13]=2[CH:14]=1)[C:7]3=4.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.[OH-].[Na+]>O1CCOCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]3[CH:19]=[CH:18][C:17](=[O:20])[C:8]4[CH:9]=[C:10]([O:15][CH3:16])[CH:11]=[C:12]([C:13]=2[CH:14]=1)[C:7]3=4

Participants

5

Reactant 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 14798Sodium HydroxideHCID 988395610-bromo-5,6-dihydro-2-methoxy-4H-pyrido[3,2,1-jk]carbazole-4-one

Product 1

HCID 2125288210-bromo-2-methoxy-4H-pyrido[3,2,1-jk]carbazole-4-oneYield 81.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

10-bromo-5,6-dihydro-2-methoxy-4H-pyrido[3,2,1-jk]carbazole-4-one (3.6 g) obtained in Example 1, step 3 was dissolved in anhydrous dioxane (300 ml), and DDQ (3.0 g) was added at room temperature. The mixture was heated under reflux in an argon atmosphere for 5 hours. After allowing to cool, the reaction mixture was added to 1N aqueous solution of sodium hydroxide (500 ml), and extracted with ethyl acetate. The ethyl acetate layer was washed with 1N aqueous solution of sodium hydroxide and saturated aqueous solution of sodium chloride in succession, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: methylene chloride containing 3% methanol) to obtain the title compound (2.9 g, 79%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux in an argon atmosphere for 5 hours
  3. temperatureto cool
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with 1N aqueous solution of sodium hydroxide and saturated aqueous solution of sodium chloride in succession
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (eluent: methylene chloride containing 3% methanol)

Sources & evidence

ORD record
ord-1d9ab0aa6f3b4d4bbbd8b505b8644ed2
Source dataset
uspto-grants-2001_03
Patent number
US06197768B1

Reaction notes

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