Maleimide → Carbazole

HRID 1165798Notes

Reaction equation

HRID 1165798 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1/[CH:10]=[CH:11]/[C:12]1[CH:17]=CC=CC=1.C1(=O)NC(=O)C=C1>C1(C)C=CC=CC=1>[CH:10]1[C:2]2[NH:1][C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[C:3]=2[CH:17]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 10935Maleimide2×HCID 11117538HCID 11117538, compound

Product 1

HCID 6854Carbazole

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1.3 g (5.9 mmole) (E)-1-(2-indolyl)-2-phenylethylene and 0.7 g (7.2 mmole) maleic acid imide are heated under reflux for 16 hours in 25 ml toluene. After the addition of 0.1 g (1 mmole) maleic acid imide, it is refluxed for a further 8 hours After cooling, the crystals formed are filtered off and chromatographed on silica gel with toluene/ethyl acetate 4:1. The fraction with the Rf of 0.1 is isolated and recrystallized from toluene. One obtains 1,2,3,3a,4,5,6,10c-octahydro-1,3-dioxo-4-phenylpyrrolo3,4-c]carbazole in the form of colorless crystals of the mp 212°-215° C.

Workup

  1. temperatureis refluxed for a further 8 hours
  2. temperatureAfter cooling
  3. customthe crystals formed
  4. filtrationare filtered off
  5. customchromatographed on silica gel with toluene/ethyl acetate 4:1
  6. customThe fraction with the Rf of 0.1 is isolated
  7. customrecrystallized from toluene

Sources & evidence

ORD record
ord-c50cef1f49cb4387a36462474be2e2ce
Source dataset
uspto-grants-1990_03
Patent number
US04912107

Reaction notes

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