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

HRID 1070568Notes

Reaction equation

HRID 1070568 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[CH3:10][N:11]1[C:15](=[O:16])[CH:14]=[CH:13][C:12]1=[O:17]>C(O)(=O)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:13]2[CH2:14][C:15](=[O:16])[N:11]([CH3:10])[C:12]2=[O:17])=[CH:2]1

Participants

4

Reactant 2

HCID 798IndoleHCID 70261N-Methylmaleimide

Product 1

HCID 153262663-(1H-indol-3-yl)-1-methylpyrrolidine-2,5-dione

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of indole (3.14 g) and N-methylmaleimide (6.2 g, 3 equiv.) in acetic acid is heated at 105° C. for 16 hr, cooled to room temperature, held for 16 hr and filtered. The filtercake is washed with acetic acid and dried to afford the title product, 5.5 g, identified by HPLC and mass spectral analyses.

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. washThe filtercake is washed with acetic acid
  4. customdried

Sources & evidence

ORD record
ord-7877840b8ab04b71bb02185f4d3c4907
Source dataset
uspto-grants-2005_06
Patent number
US06903112B2

Reaction notes

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