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

HRID 1017573Notes

Reaction equation

HRID 1017573 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:26])O[C:14](=[O:25])[C:15]=2[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-:24])=[O:23])[CH:17]=2)=[CH:3]1.[NH3:27].O>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:26])[NH:27][C:14](=[O:25])[C:15]=2[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-:24])=[O:23])[CH:17]=2)=[CH:3]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 962WaterHCID 18403563HCID 18403563, compound

Product 1

HCID 53277123-(1-methyl-1H-indol-3-yl)-4-(3-nitrophenyl)-2,5-dihydro-1H-pyrrole-2,5-dioneYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-(1-methylindol-3-yl)-4-(3-nitrophenyl)furan-2,5-dione (9 g, 26 mmol) in DMF (20 mL) was heated to about 140° C. Aqueous ammonia (20 mL) was added in portions and the heating was continued for 6 h. Water (20 mL) was added and the reaction mixture was allowed to stand at room temperature overnight. The orange colored solid was filtered off, washed with water and dried under vacuum to afford 3-(1-methylindol-3-yl)-4-(3-nitrophenyl)-1H-pyrrole-2,5-dione (6.7 g, 75%).

Workup

  1. waitto stand at room temperature overnight
  2. filtrationThe orange colored solid was filtered off
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-3e76bb2b8a2b474cb144402172194765
Source dataset
uspto-grants-2002_11
Patent number
US06479490B2

Reaction notes

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