Water → HCID 12805226, compound

HRID 1906226Notes

Reaction equation

HRID 1906226 reaction equation
[H-].[Na+].[O:3]=[C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](=[O:13])[N:5]1[CH2:14][CH2:15][C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([CH2:25][C:26]([NH2:28])=[O:27])[CH:23]=2)[NH:18][CH:17]=1.[CH3:29]I.O>CN(C)C=O>[O:3]=[C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](=[O:13])[N:5]1[CH2:14][CH2:15][C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([CH2:25][C:26]([NH2:28])=[O:27])[CH:23]=2)[N:18]([CH3:29])[CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 12805213HCID 12805213, compound

Product 1

HCID 12805226HCID 12805226, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (80% dispersion in oil) (0.14 g) was added to a solution of 3-[2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)ethyl]-1H-indole-5-acetamide (1.5 g) in dry dimethylformamide (10 ml). After stirring the red solution for 30 min, methyl iodide (0.41 ml) was added and the mixture was stirred for a further 16 h. Water (40 ml) was added, the solid collected by filtration and crystallised from propan-2-ol to give the title compound as a yellow powder (1.25 g), m.p. 200°-2° C.

Workup

  1. stirringthe mixture was stirred for a further 16 h
  2. filtrationthe solid collected by filtration
  3. customcrystallised from propan-2-ol

Sources & evidence

ORD record
ord-bac3cb49488f4f389cfcfc22f95c3eaf
Source dataset
uspto-grants-1987_03
Patent number
US04650810

Reaction notes

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