Water → N-[2-(3-acetyl-1H-indol-1-yl)-ethyl]-1H-isoindole-1,3(2H)-dione

HRID 976275Notes

Reaction equation

HRID 976275 reaction equation
[C:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1)(=[O:3])[CH3:2].[H-].[Na+].Br[CH2:16][CH2:17][N:18]1[C:22](=[O:23])[C:21]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]2[C:19]1=[O:28].O>CN(C)C=O>[C:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([CH2:16][CH2:17][N:18]2[C:19](=[O:28])[C:20]3[C:21](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]2=[O:23])[CH:5]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-HCID 128023-AcetylindoleHCID 24758Sodium hydride

Product 1

HCID 19967013N-[2-(3-acetyl-1H-indol-1-yl)-ethyl]-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.5 g (15.7 mmol) of 3-acetyl-1H-indole are dissolved in 100 ml of dimethylformamide, and 0.41 g (15.7 mmol) of sodium hydride and 4.0 g (16 mmol) of N-(2-bromo-ethyl)-phthalimide are added. The reaction mixture is stirred for 14 h at RT and for 3 h at 50°. 20 ml of water are added and the product is isolated by filtration. After drying at 50° under HV, N-[2-(3-acetyl-1H-indol-1-yl)-ethyl]-1H-isoindole-1,3(2H)-dione is obtained; 1H-NMR (CDCl3): 2.5 (3H,s), 4.1 (2H,t), 4.45 (2H,t), 7.2-7.9 (8H,m), 8.35 (1H n).

Workup

  1. customthe product is isolated by filtration
  2. customAfter drying at 50° under HV

Sources & evidence

ORD record
ord-e7a1ed14236a4937b89ac6c580f15b7e
Source dataset
uspto-grants-1997_03
Patent number
US05612340

Reaction notes

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