2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 3-Fluoro-8-methoxy-6,6-dimethyl-5,6-dihydro-benzo[b]carbazol-11-one

HRID 2275233Notes

Reaction equation

HRID 2275233 reaction equation
[CH2:1]1[CH2:5][O:4][CH2:3][CH2:2]1.[F:6][C:7]1[CH:19]=[C:18]2[C:10]([C:11]3C[C:13]4C=C[C:23]([O:26]C)=[CH:22][C:14]=4[C:15]([CH3:21])([CH3:20])[C:16]=3[NH:17]2)=[CH:9][CH:8]=1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.[OH-].[Na+]>C(OCC)C.O>[F:6][C:7]1[CH:19]=[C:18]2[C:10]([C:11]3[C:23](=[O:26])[C:22]4[CH:2]=[CH:1][C:5]([O:4][CH3:3])=[CH:13][C:14]=4[C:15]([CH3:20])([CH3:21])[C:16]=3[NH:17]2)=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 66834755HCID 66834755, compound

Product 1

HCID 668346943-Fluoro-8-methoxy-6,6-dimethyl-5,6-dihydro-benzo[b]carbazol-11-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

Under nitrogen atmosphere, to the THF (1.8 mL)-water (0.18 mL) solution of 3-fluoro-8-methoxy-6,6-dimethyl-6,11-dihydro-5H-benzo[b]carbazole (Compound V2, 72.4 mg, 0.245 mmol), DDQ (122.4 mg, 0.539 mmol) was added and the mixture was stirred at room temperature for 5 hr. The reaction mixture was added with diethyl ether and 0.5 N aqueous solution of sodium hydroxide (2 mL), and the resulting mixture was extracted twice with diethyl ether. The organic layer was washed twice with 0.5 N aqueous solution of sodium hydroxide (2 mL) and subsequently twice with brine (2 mL), and dried over sodium sulfate. After concentration under reduced pressure, hexane/ethyl acetate (5:1) and diethyl ether were added to the obtained crude product, and the solid was triturated. After removing the supernatant and drying under reduced pressure, the title compound was obtained (yellow solid, 57.0 mg, 75%).

Workup

  1. extractionthe resulting mixture was extracted twice with diethyl ether
  2. washThe organic layer was washed twice with 0.5 N aqueous solution of sodium hydroxide (2 mL) and subsequently twice with brine (2 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationAfter concentration under reduced pressure, hexane/ethyl acetate (5:1) and diethyl ether
  5. additionwere added to the
  6. customobtained crude product
  7. customthe solid was triturated
  8. customAfter removing the supernatant
  9. customdrying under reduced pressure

Sources & evidence

ORD record
ord-1501a6272f824bd59742a09371aabe17
Source dataset
uspto-grants-2015_09
Patent number
US09126931B2

Reaction notes

Loading…