Maleimide, N-p-tolyl- → HCID 19808813, compound

HRID 374008Notes

Reaction equation

HRID 374008 reaction equation
[CH2:1]=[C:2]([C:5]1[N:6]([CH2:16][O:17][CH3:18])[C:7]2[C:12]([CH:13]=1)=[CH:11][C:10]([O:14][CH3:15])=[CH:9][CH:8]=2)[CH2:3][CH3:4].[CH3:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]2[C:30](=[O:31])[CH:29]=[CH:28][C:27]2=[O:32])=[CH:22][CH:21]=1>C1(C)C(C)=CC=CC=1>[CH3:19][C:20]1[CH:21]=[CH:22][C:23]([N:26]2[C:30](=[O:31])[CH:29]3[CH:28]([CH2:1][CH:2]([CH2:3][CH3:4])[C:5]4[N:6]([CH2:16][O:17][CH3:18])[C:7]5[C:12]([C:13]=43)=[CH:11][C:10]([O:14][CH3:15])=[CH:9][CH:8]=5)[C:27]2=[O:32])=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 15399Maleimide, N-p-tolyl-HCID 19808724HCID 19808724, compound

Product 1

HCID 19808813HCID 19808813, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

5 ml of xylene was added to a mixture of 580 mg of 2-(1-buten-2-yl)-5-methoxy-1-methoxymethylindole and 880 mg of N-(4-methylphenyl)maleimide. The mixture was refluxed for 1.5 hours. The solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography (eluant: n-hexane/ethyl acetate=5/1 to 2/1) to obtain 510 mg (yield: 50%) of N-(4-methylphenyl)-1-ethyl-6-methoxy-9-methoxymethyl-1,2,3,4-tetrahydrocarbazole-3,4-dicarboximide as colorless crystals.

Workup

  1. temperatureThe mixture was refluxed for 1.5 hours
  2. customThe solvent was removed by distillation under reduced pressure
  3. customThe residue was purified by column chromatography (eluant: n-hexane/ethyl acetate=5/1 to 2/1)

Sources & evidence

ORD record
ord-2f3746aeb07a4bef9d11b2e8c27a64a3
Source dataset
uspto-grants-1992_11
Patent number
US05166204

Reaction notes

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