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Dimethylformamide → 2-[(6-Chloropyridin-3-yl)methyl]-1H-isoindole-1,3(2H)-dione

HRID 249469
Notes
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Reaction equation

HRID 249469 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[OH-].[K+].CN(C)C=O.[Cl:19][C:20]1[N:25]=[CH:24][C:23]([CH2:26]Cl)=[CH:22][CH:21]=1>CCO>[Cl:19][C:20]1[N:25]=[CH:24][C:23]([CH2:26][N:5]2[C:1](=[O:11])[C:2]3=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]3[C:4]2=[O:6])=[CH:22][CH:21]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6809PhthalimideHCID 14797Potassium HydroxideHCID 1554792-Chloro-5-(chloromethyl)pyridine

Product 1

HCID 143247132-[(6-Chloropyridin-3-yl)methyl]-1H-isoindole-1,3(2H)-dioneYield 98.3%

Reagents, catalysts & solvents 1

HCID 702
Ethanol
Solvent

Conditions

Temperature
60 °C

Procedure

In 20 ml of EtOH, 9.4 g (6.4×10-2 mole) of phthalimide and 4.2 g of KOH were stirred for 30 minutes, followed by addition of 100 ml of DMF (dimethylformamide) and 5.2 g (2.5×10-2 mole) of 6-chloro-3-pyridylmethyl chloride. The mixture was stirred at 60° C. for 1 hour. The EtOH and DMF were distilled off under reduced pressure and the residue was chromatographed on a silica gel column and eluted with CH2Cl2. The above procedure gave 6.7 g of the title compound as colorless needles.

Workup

  1. distillationThe EtOH and DMF were distilled off under reduced pressure
  2. customthe residue was chromatographed on a silica gel column
  3. washeluted with CH2Cl2

Sources & evidence

ORD record
ord-69b35144e0ef4190b4e807ad45adfdeb
Source dataset
uspto-grants-1993_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05214152

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes