1-Iodonaphthalene → 5,11-Di-1-naphthyl-5,11-dihydroindolo[3,2-b]carbazole

HRID 1585962Notes

Reaction equation

HRID 1585962 reaction equation
[CH:1]1[CH:6]=[CH:5][CH:4]=[C:3]2[NH:7][C:8]3[C:9](=[CH:10][C:11]4[NH:12][C:13]5[C:18]([C:19]=4[CH:20]=3)=[CH:17][CH:16]=[CH:15][CH:14]=5)[C:2]=12.I[C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+].CCC[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH3:50]>O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2].O.C1(C)C=CC=CC=1>[C:22]1([N:12]2[C:11]3[C:19](=[CH:20][C:8]4[N:7]([C:41]5[C:42]6[C:47](=[CH:46][CH:45]=[CH:44][CH:43]=6)[CH:48]=[CH:49][CH:50]=5)[C:3]5[C:2]([C:9]=4[CH:10]=3)=[CH:1][CH:6]=[CH:5][CH:4]=5)[C:18]3[C:13]2=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24][CH:23]=1

Participants

8

Reactant 4

HCID 70041-IodonaphthaleneHCID 11430Potassium CarbonateHCID 12388TridecaneHCID 958385,11-Dihydroindolo[3,2-b]carbazole

Product 1

HCID 225985955,11-Di-1-naphthyl-5,11-dihydroindolo[3,2-b]carbazole

Reagents, catalysts & solvents 3

HCID 24463Copper sulfate pentahydrateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
250 °C

Procedure

A 200 milliliter 3-necked round bottom flask equipped with a mechanical stirrer, reflux condenser, and argon inlet was purged with argon and then charged with 5,11-dihydroindolo[3,2-b]carbazole (5.1 grams, 0.02 mol), 1-iodonaphthalene (10.16 grams, 0.04 mol), copper sulfate pentahydrate (0.25 gram, 1.0 mmol), potassium carbonate (5.52 grams, 0.04 mol), and n-tridecane (5.0 milliliters). Under an argon atmosphere, the reaction mixture was heated to about 250° C. with a heating mantle and allowed to proceed at this temperature to completion in about 6 hours. The reaction mixture was cooled to about 100° C., and 100 milliliters of toluene and 15 milliliters of water were then added with vigorous stirring for 30 minutes. The resulting two phase mixture was transferred into a separatory funnel and the layers separated. The organic phase, which contains the desired product and the solvent mixture, were washed with water, treated under argon with 25 grams of alumina, and filtered. The filtrate was evaporated and the residue was recrystallized from toluene to provide 2.5 grams of pure, about 99.5 percent, 5,11-di-1-naphthyl-5,11-dihydroindolo[3,2-b]carbazole (3).

Workup

  1. customA 200 milliliter 3-necked round bottom flask equipped with a mechanical stirrer
  2. temperaturereflux condenser, and argon inlet
  3. customwas purged with argon
  4. temperatureThe reaction mixture was cooled to about 100° C.
  5. customThe resulting two phase mixture was transferred into a separatory funnel
  6. customthe layers separated
  7. washthe solvent mixture, were washed with water
  8. additiontreated under argon with 25 grams of alumina
  9. filtrationfiltered
  10. customThe filtrate was evaporated
  11. customthe residue was recrystallized from toluene

Sources & evidence

ORD record
ord-5049e56de4b94f978f52df2ad2d7a5ef
Source dataset
uspto-grants-1999_08
Patent number
US05942340

Reaction notes

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