Ammonia → 3-(1-methyl-1H-indol-3-yl)-4-(1-phenyl-1H-indol-3-yl)-2,5-dihydro-1H-pyrrole-2,5-dione

HRID 1421174Notes

Reaction equation

HRID 1421174 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[C:12](=[O:32])[O:13][C:14](=O)[C:15]=2[C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:17]=2)=[CH:3]1.[NH3:33]>CN(C=O)C>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]2[C:12](=[O:32])[NH:33][C:14](=[O:13])[C:15]=2[C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:17]=2)=[CH:3]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 18780269HCID 18780269, compound

Product 1

HCID 53276583-(1-methyl-1H-indol-3-yl)-4-(1-phenyl-1H-indol-3-yl)-2,5-dihydro-1H-pyrrole-2,5-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

150 mg of 3-(1-methyl-3-indolyl)-4-(1-phenyl-3-indolyl)furan-2,5-dione were treated with 3 ml of DMF and 10 ml of 33% aqueous ammonia at 80° C. for 4 hours. The mixture was cooled and extracted with ethyl acetate. The ethyl acetate extract was dried and concentrated. The residue was crystallized from ethyl acetate/hexane to give 120 mg of 3-(1-methyl-3-indolyl)-4-(1-phenyl-3-indolyl)-1H-pyrrole-2,5-dione, m.p. 135°-137° C.

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with ethyl acetate
  3. extractionThe ethyl acetate extract
  4. customwas dried
  5. concentrationconcentrated
  6. customThe residue was crystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-8aa036fb6a064b10aef46a0c7b8b1de4
Source dataset
uspto-grants-2000_06
Patent number
USRE036736

Reaction notes

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