Maleimide → 4c,7a,7b,12a-Tetrahydro-6H,12H,13H-indeno[2,3-a]pyrrolo[3,4-c]carbazole-5,7-(5H, 7H)dione

HRID 1279505Notes

Reaction equation

HRID 1279505 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]1[NH:11][C:12]2[C:17]([CH:18]=1)=[CH:16][CH:15]=[CH:14][CH:13]=2.[C:19]1(=[O:25])[NH:23][C:22](=[O:24])[CH:21]=[CH:20]1>CO>[CH:5]1[C:4]2[CH2:3][C:2]3[CH:10]4[CH:18]([C:17]5[C:12]([NH:11]4)=[CH:13][CH:14]=[CH:15][CH:16]=5)[CH:21]4[C:22](=[O:24])[NH:23][C:19](=[O:25])[CH:20]4[C:1]=3[C:9]=2[CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 10935MaleimideHCID 105856192-(2Indenyl)indole

Product 1

HCID 178780994c,7a,7b,12a-Tetrahydro-6H,12H,13H-indeno[2,3-a]pyrrolo[3,4-c]carbazole-5,7-(5H, 7H)dioneYield 62.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-(2-indenyl)indole (1.0 g, 4.3 mmol) and maleimide (525 mg, 5.41 mmol) in a 10 cm sealed reaction vial was heated at 180°-190° C. for 30 min. After cooling the reaction to ambient temperature, MeOH (5 mL) was added. The product was collected to give 880 mg (62%) of a white solid product with a m.p. of 254°-255° C. (MeOH). The following NMR data were obtained: 1H NMR (DMSO-d6, 300 MHz): 63.1-3.4 (m, 2H), 3.8 (m, 2H), 3.95 (t, 1H), 4.35 (d, 1H), 6.9-7.4 (m, 7H), 7.75 (d, 1H), 11.05 (s, 1H), 11.25 (s, 1H).

Workup

  1. customsealed
  2. customreaction
  3. temperaturevial was heated at 180°-190° C. for 30 min
  4. temperatureAfter cooling
  5. customthe reaction to ambient temperature
  6. customThe product was collected

Sources & evidence

ORD record
ord-8c84780f43594822a40c42661abc35f2
Source dataset
uspto-grants-2002_09
Patent number
US06448283B1

Reaction notes

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