Sodium Hydroxide → 3-Butyl-1-methyl-4-(1-methylindol-3-yl)pyrrole-2,5-dione

HRID 1168659Notes

Reaction equation

HRID 1168659 reaction equation
CC(C)C(N)=O.[OH-].[Na+].CN1C2C(=CC=CC=2)C(C2C(=O)N(C)C(=O)C=2Cl)=C1.[CH3:28][N:29]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:31]([C:38]2[C:43](=[O:44])[N:42]([CH3:45])[C:40](=[O:41])[C:39]=2[C:46]2C=C[CH:49]=[CH:48][CH:47]=2)=[CH:30]1.Cl.O>O>[CH3:49][CH2:48][CH2:47][CH2:46][C:39]1[C:40](=[O:41])[N:42]([CH3:45])[C:43](=[O:44])[C:38]=1[C:31]1[C:32]2[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:29]([CH3:28])[CH:30]=1

Participants

7

Reactant 5

HCID 14798Sodium HydroxideHCID 68424Isobutyramide2×HCID 178316153-Chloro-1-methyl-4-(1-methylindol-3-yl)pyrrole-2,5-dioneHCID 178436842-(1-methyl-1H-indol-3-yl)-3-phenyl-N-methylmaleimideHCID 21885828Hydrate;hydrochloride

Product 1

HCID 1022626083-Butyl-1-methyl-4-(1-methylindol-3-yl)pyrrole-2,5-dioneYield 85.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into dimethylacetoamide (30 ml) was dispersed sodium hydroxide (content: 60%, 0.88 g, 22 mmol). To this were added IM-3 obtained in Example 1-2 (1.77 g, 10 mmol)/dimethylacetoamide (5 ml). This mixture was stirred for 10 minutes, then, to this was added IM-5 (4.5 g, 11 mmol) obtained as described above, and this mixture was stirred for three hours. To this was added water (10 ml), and this mixture was acidified with 1N water hydrochloride, and the reaction solution was concentrated. The concentrated mixture was refined with silica gel column chromatography to obtain 2.8 g of IM-6.

Workup

  1. customobtained
  2. stirringwas stirred for three hours
  3. concentrationthe reaction solution was concentrated

Sources & evidence

ORD record
ord-9385340d53934a99add929f6a0125ba7
Source dataset
uspto-grants-2003_09
Patent number
US06627099B2

Reaction notes

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