Indole → 3-(1H-indol-3-yl)pyrrolidine-2,5-dione

HRID 2357428Notes

Reaction equation

HRID 2357428 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[C:10]1(=[O:16])[NH:14][C:13](=[O:15])[CH:12]=[CH:11]1.O>C(O)(=O)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:12]2[CH2:11][C:10](=[O:16])[NH:14][C:13]2=[O:15])=[CH:2]1

Participants

5

Reactant 3

HCID 798IndoleHCID 962WaterHCID 10935Maleimide

Product 1

HCID 3633263-(1H-indol-3-yl)pyrrolidine-2,5-dione

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Indole (4.38 g, 40 mmole) and maleimide (7.84 g, 80 mmole) were dissolved in concentrated acetic acid (35 ml) and stirred under reflux for 36 hours. After cooling the reaction mixture water (10 ml) was slowly added dropwise. The solution was then kept for 24 hours in a refrigerator. The solid thereby formed was filtered off. 3-(1H-indol-3-yl)-pyrrolidine-2,5-dione was thereby obtained as a brown solid in a yield of 3.24 g (38%).

Workup

  1. temperatureunder reflux for 36 hours
  2. additionwas slowly added dropwise
  3. customThe solid thereby formed
  4. filtrationwas filtered off

Sources & evidence

ORD record
ord-a4d7e3f2c9f74075a4fa0724ba3d4650
Source dataset
uspto-grants-2010_07
Patent number
US07759385B2

Reaction notes

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