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Ammonia → 3-(1-methyl-3-indolyl)-4-(4-pyridyl)-1H-pyrrole-2,5-dione

HRID 1421184
Notes
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Reaction equation

HRID 1421184 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:23])O[C:14](=[O:22])[C:15]=2[C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)=[CH:3]1.C[N:25](C=O)C.N>O>[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:23])[NH:25][C:14](=[O:22])[C:15]=2[C:16]2[CH:17]=[CH:18][N:19]=[CH:20][CH:21]=2)=[CH:3]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 222AmmoniaHCID 6228DimethylformamideHCID 187802473-(1-Methyl-3-indolyl)-4-(4-pyridyl)furan-2,5-dione

Product 1

HCID 187802743-(1-methyl-3-indolyl)-4-(4-pyridyl)-1H-pyrrole-2,5-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

200 mg of 3-(1-methyl-3-indolyl)-4-(4-pyridyl)furan-2,5-dione were treated with 5 ml of DMF and 5 ml of 33% aqueous ammonia. The resulting solution was heated at 140° C. for 17 hours. After cooling, the suspension was diluted with water. The product was filtered off, washed with water and dried to give 144 mg of 3-(1-methyl-3-indolyl)-4-(4-pyridyl)-1H-pyrrole-2,5-dione, m.p. 332°-334° C.

Workup

  1. temperatureAfter cooling
  2. filtrationThe product was filtered off
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-bc7bf9e421254f168562f45ce5fd372f
Source dataset
uspto-grants-2000_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
USRE036736

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes