Benzene → 10,11,11-triphenyl-11H-indeno[1,2-b]quinoline

HRID 713587Notes

Reaction equation

HRID 713587 reaction equation
[C:1]1([C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[C:9]3[C:17]4[C:22]([C:23]([C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=5)(O)[C:8]=23)=[CH:21][CH:20]=[CH:19][CH:18]=4)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.FC(F)(F)S(O)(=O)=O>ClCCl>[C:1]1([C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[C:9]3[C:17]4[C:22]([C:23]([C:31]5[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=5)([C:25]5[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=5)[C:8]=23)=[CH:21][CH:20]=[CH:19][CH:18]=4)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 241BenzeneHCID 62406Trifluoromethanesulfonic acidHCID 11760624810,11-diphenyl-11H-indeno[1,2-b]quinolin-11-ol

Product 1

HCID 11760624310,11,11-triphenyl-11H-indeno[1,2-b]quinolineYield 91.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In all embodiment, the starting material 10,11-diphenyl-11H-indeno[1,2-b]quinolin-11-ol (385 mg, 2.50 mmol) and benzene (1430 mg, 18.31 mmol) are placed in a round bottom flask and then dissolved in 10 ml of dichloromethane. Subsequently, trifluoromethanesulfonic acid (0.09 ml, 1.10 mmol) is slowly dripped into the flask to promote reaction. After 12 hours of reaction at 140° C., the crude product is extracted with 50 ml of Ethyl acetate and sodium bicarbonate for three times. Finally, an organic layer of the crude product is dehydrated with magnesium sulfate and concentrated to be sublimated and purified to obtain 281 mg of 10,11,11-triphenyl-11H-indeno[1,2-b]quinoline. The percentage yield is 91.7%.

Workup

  1. customreaction
  2. customAfter 12 hours of reaction at 140° C.
  3. extractionthe crude product is extracted with 50 ml of Ethyl acetate and sodium bicarbonate for three times
  4. concentrationconcentrated
  5. custompurified

Sources & evidence

ORD record
ord-d24a53de98e54f2aad73f7a640612a2c
Source dataset
uspto-grants-2015_11
Patent number
US09184396B2

Reaction notes

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