Water → HCID 17855555, compound

HRID 732286Notes

Reaction equation

HRID 732286 reaction equation
[C:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][NH:10]2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[OH2:13]>C(#N)C>[C:1]([C:4]1[CH:12]=[C:11]2[C:7]([C:8]3[C:9]([NH:10]2)=[C:9]2[NH:10][C:11]4[CH:12]=[C:4]([C:1](=[O:13])[CH3:2])[CH:5]=[CH:6][C:7]=4[C:8]2=[C:9]2[NH:10][C:11]4[CH:12]=[C:4]([C:1](=[O:3])[CH3:2])[CH:5]=[CH:6][C:7]=4[C:8]=32)=[CH:6][CH:5]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 962WaterHCID 129250701-(1H-Indol-6-yl)ethan-1-one2×

Product 1

HCID 17855555HCID 17855555, compoundYield 70.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

15 ml of acetonitrile was poured into a 200 ml three-neck flask, and 1.59 g of 6-acetylindole was dissolved therein. On the other hand, preparation of an oxidant solution was performed by dissolving 16.2 g of ferric chloride anhydrate and 5.4 g of water in 100 ml of acetonitrile and agitating the resultant mixture solution for 15 minutes. Then, the prepared 6-acetyl indole solution was dripped over 60 minutes into the oxidant solution, and the resultant mixture solution was agitated for 5 hours at the temperature of 30° C. Color of the reaction solution changed from yellow to blue-green with slight heat generation. pH of the reaction solution was less than 1. After the end of the reaction, the reaction liquid was suction-filtered with a perforated funnel, and the filtrate was washed with acetonitrile and then methanol, and was dried to obtain 1.11 g of 3,8,13-triacetyl-6,11-dihydro-5H-diindolo [2,3-a:2′,3′-c] carbazole (6-acetyl indole trimer) with a blue-green color (yield: 70%). The resultant trimer was pressure-molded with a tablet molding machine and the mold was cut into a piece with the diameter of 10 mm and thickness of 1 mm. A conductivity thereof was measured by the four terminal method and found to be 0.90 S/cm. The result of elemental analysis was: <C10.00H6.99N0.98O1.98Cl0.10>3.

Workup

  1. customOn the other hand, preparation of an oxidant solution
  2. customAfter the end of the reaction
  3. customthe reaction liquid
  4. filtrationwas suction-filtered with a perforated funnel
  5. washthe filtrate was washed with acetonitrile
  6. dry with materialmethanol, and was dried

Sources & evidence

ORD record
ord-51d2c72407fb45bd9d7159a7cc5b152c
Source dataset
uspto-grants-2009_09
Patent number
US07585981B2

Reaction notes

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