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

HRID 61862Notes

Reaction equation

HRID 61862 reaction equation
[O:1]1CCOCC1.[Cl:7][C:8]1[CH:9]=[C:10]2[C:18](=[CH:19][C:20]=1[Cl:21])[NH:17][C:16]1[C:15]([CH3:23])([CH3:22])[C:14]3[CH:24]=[C:25]([O:28][CH3:29])[CH:26]=[CH:27][C:13]=3[CH2:12][C:11]2=1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>O>[Cl:7][C:8]1[CH:9]=[C:10]2[C:18](=[CH:19][C:20]=1[Cl:21])[NH:17][C:16]1[C:15]([CH3:22])([CH3:23])[C:14]3[CH:24]=[C:25]([O:28][CH3:29])[CH:26]=[CH:27][C:13]=3[C:12](=[O:1])[C:11]2=1

Participants

5

Reactant 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 312751,4-DioxaneHCID 668349922,3-Dichloro-8-methoxy-6,6-dimethyl-6,11-dihydro-5H-benzo[b]carbazole

Product 1

HCID 668343702,3-Dichloro-8-methoxy-6,6-dimethyl-5,6-dihydro-benzo[b]carbazol-11-oneYield 26%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under nitrogen atmosphere, to the 1,4-dioxane (1.7 mL)-water (0.1 mL) solution of 2,3-dichloro-8-methoxy-6,6-dimethyl-6,11-dihydro-5H-benzo[b]carbazole (Compound Y2, 61.0 mg, 0.176 mmol), DDQ (120 mg, 0.529 mmol) was added and the mixture was stirred at room temperature for 16 hr and 15 min. The reaction mixture was purified by flash column chromatography {Merck Kieselgel60, solution for elution:hexane/ethyl acetate (2:1)} to obtain the title compound (pale orange solid, 16.7 mg, 26%).

Workup

  1. customThe reaction mixture was purified by flash column chromatography {Merck Kieselgel60, solution for elution

Sources & evidence

ORD record
ord-95cdca1b5be345edb37e947d05c380b3
Source dataset
uspto-grants-2016_09
Patent number
US09440922B2

Reaction notes

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