9-(p-Tolyl)carbazole → 10,11-diphenyl-11-(9-(p-tolyl)-9H-carbazol-3-yl)-11H-indeno[1,2-b]quinoline

HRID 713585Notes

Reaction equation

HRID 713585 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.[C:31]1([CH3:50])[CH:36]=[CH:35][C:34]([N:37]2[C:49]3[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=3[C:43]3[C:38]2=[CH:39][CH:40]=[CH:41][CH:42]=3)=[CH:33][CH:32]=1.CS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=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:25]5[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=5)([C:41]5[CH:40]=[CH:39][C:38]6[N:37]([C:34]7[CH:33]=[CH:32][C:31]([CH3:50])=[CH:36][CH:35]=7)[C:49]7[C:44]([C:43]=6[CH:42]=5)=[CH:45][CH:46]=[CH:47][CH:48]=7)[C:8]=23)=[CH:21][CH:20]=[CH:19][CH:18]=4)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 157986519-(p-Tolyl)carbazoleHCID 86584057Phosphorus Pentoxide-Methanesulfonic AcidHCID 11760624810,11-diphenyl-11H-indeno[1,2-b]quinolin-11-ol

Product 1

HCID 11760624610,11-diphenyl-11-(9-(p-tolyl)-9H-carbazol-3-yl)-11H-indeno[1,2-b]quinolineYield 83.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Referring to the reaction formula above, 10,11-diphenyl-11H-indeno[1,2-b]quinolin-11-ol (385 mg, 1.00 mmol) and 9-(p-tolyl)-9H-carbazole (291 mg, 1.20 mmol) are placed in a round bottom flask and then dissolved in 5 ml of dichloromethane. Subsequently, 286 of Eaton's reagent is slowly dripped into the flask to promote reaction. After 12 hours of reaction at 100° C., the crude product is extracted with 8 ml of dichloromethane 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 521 mg of 10,11-diphenyl-11-(9-(p-tolyl)-9H-carbazol-3-yl)-11H-indeno[1,2-b]quinoline. The percentage yield is 83.4%.

Workup

  1. customare placed in a round bottom flask
  2. customreaction
  3. customAfter 12 hours of reaction at 100° C.
  4. extractionthe crude product is extracted with 8 ml of dichloromethane and sodium bicarbonate for three times
  5. concentrationconcentrated
  6. custompurified

Sources & evidence

ORD record
ord-ede88c5e066940a39e26a56ea8189a46
Source dataset
uspto-grants-2015_11
Patent number
US09184396B2

Reaction notes

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