Sodium Hydroxide → Iron oxide, spent

HRID 1017574Notes

Reaction equation

HRID 1017574 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])[NH:13][C:14](=[O:25])[C:15]=2[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-])=O)[CH:17]=2)=[CH:3]1.[OH-].[Na+]>CC(C)=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:26])[NH:13][C:14](=[O:25])[C:15]=2[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([NH2:22])[CH:17]=2)=[CH:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 53277123-(1-methyl-1H-indol-3-yl)-4-(3-nitrophenyl)-2,5-dihydro-1H-pyrrole-2,5-dione

Product 1

HCID 5327711Iron oxide, spentYield 82.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 3-(1-methylindol-3-yl)-4-(3-nitrophenyl)-1H-pyrrole-2,5-dione (6.5 g, 19 mmol) in acetone (500 mL), was added TiCl3 (45 mL) in 5 portions at 30 minute interval. The reaction mixture was stirred at room temperature overnight and then neuteralized with 10N NaOH. The product was extracted with EtOAc, dried, and concentrated. The crude product was purified on a silica gel column with 3% MeOH in CH2Cl2 to afford 3-(1-methylindol-3-yl)-4-(3-aminophenyl)-1H-pyrrole-2,5-dione (4.9 g, 82.5%).

Workup

  1. extractionThe product was extracted with EtOAc
  2. customdried
  3. concentrationconcentrated
  4. customThe crude product was purified on a silica gel column with 3% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-7ec3f3ad7e174ffc8e563c1b37602611
Source dataset
uspto-grants-2002_11
Patent number
US06479490B2

Reaction notes

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