Water → 6,11-dihydro-5H-diindolo[2,3-a:2',3'-c]carbazole-2,9,14-tricarboxylic acid
Reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([OH:12])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[OH2:13]>C(#N)C>[CH:5]1[C:6]([C:10]([OH:12])=[O:11])=[CH:7][CH:8]=[C:9]2[C:4]=1[C:3]1[C:2]([NH:1]2)=[C:2]2[NH:1][C:9]3[CH:8]=[CH:7][C:6]([C:10]([OH:13])=[O:13])=[CH:5][C:4]=3[C:3]2=[C:2]2[NH:1][C:9]3[CH:8]=[CH:7][C:6]([C:10]([OH:12])=[O:11])=[CH:5][C:4]=3[C:3]=12Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
10 ml of acetonitrile were placed in a 200 ml three-mouth flask followed by dissolving 1.42 g of indole-5-carboxylic acid. On the other hand, preparation of the oxidizing agent solution was carried out by dissolving 16.2 g of anhydrous ferric chloride and 5.4 g of water in 40 ml of acetonitrile and stirring for 10 minutes. Next, after dropping in the prepared oxidizing agent solution into the aqueous indole-5-carboxylic acid solution over the course of 30 minutes, the solution was stirred for 10 hours at 60° C. The reaction solution changed from a pale yellow color to a light green color while generating a small amount of heat, and its pH was 1 or less. Following completion of the reaction, the reaction solution was aspiration filtered with a Kiriyama funnel, washed with acetonitrile and then methanol and dried to obtain 1.12 g of light green 6,11-dihydro-5H-diindolo[2,3-a:2′,3′-c]carbazole-2,9,14-tricarboxylic acid (indole-5-carboxylic acid trimer) (yield: 79%).
Workup
- customOn the other hand, preparation of the oxidizing agent solution
- stirringthe solution was stirred for 10 hours at 60° C
- temperatureof heat
- customcompletion of the reaction
- filtrationaspiration filtered with a Kiriyama funnel
- washwashed with acetonitrile
- dry with materialmethanol and dried
Sources & evidence
- ORD record
- ord-f43f1b1e59444c59a678a04097b9529e
- Source dataset
- uspto-grants-2010_01
- Patent number
- US07645400B2
Reaction notes
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