3,4-Bis-(1-methyl-6-nitro-1H-indol-3-yl)-pyrrole-2,5-dione → HCID 21999014, compound

HRID 1976734Notes

Reaction equation

HRID 1976734 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N+:11]([O-])=O)[CH:9]=2)[C:4]([C:14]2[C:15](=[O:33])[NH:16][C:17](=[O:32])[C:18]=2[C:19]2[C:27]3[C:22](=[CH:23][C:24]([N+:28]([O-])=O)=[CH:25][CH:26]=3)[N:21]([CH3:31])[CH:20]=2)=[CH:3]1>CN(C)C=O.[Ni]>[CH3:31][N:21]1[C:22]2[C:27](=[CH:26][CH:25]=[C:24]([NH2:28])[CH:23]=2)[C:19]([C:18]2[C:17](=[O:32])[NH:16][C:15](=[O:33])[C:14]=2[C:4]2[C:5]3[C:10](=[CH:9][C:8]([NH2:11])=[CH:7][CH:6]=3)[N:2]([CH3:1])[CH:3]=2)=[CH:20]1

Participants

4

Reactant 1

HCID 117751473,4-Bis-(1-methyl-6-nitro-1H-indol-3-yl)-pyrrole-2,5-dione

Product 1

HCID 21999014HCID 21999014, compoundYield 82.6%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 6228DimethylformamideSolvent

Procedure

3,4-Bis-(1-methyl-6-nitro-1H-indol-3-yl)-pyrrole-2,5-dione (50 mg, 0.11 mmole), as prepared in Example 2 g, was dissolved in N,N-dimethylformamide (10 mL), a catalytic amount of activated Raney Nickel was added and the reaction was shaken on a Parr Hydro-genator at 45 psi. for 20 hr. The reaction mixture was filtered through a bed of celite with ethyl acetate and concentrated. The product was purified by recrystallization from acetone and hexane to give 3,4-bis-(1-methyl-6-amino-1H-indol-3-yl)-pyrrole-2,5-dione (35 mg).

Workup

  1. filtrationThe reaction mixture was filtered through a bed of celite with ethyl acetate
  2. concentrationconcentrated
  3. customThe product was purified by recrystallization from acetone and hexane

Sources & evidence

ORD record
ord-f964edef462e4e3a887bd19a54da415d
Source dataset
uspto-grants-2001_05
Patent number
US06228877B1

Reaction notes

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