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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 249469Generated: October 30, 2026

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

https://huagongshe.com/reaction/249469

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
ReactantPhthalimideHCID 6809—
ReactantPotassium HydroxideHCID 14797—
Reactant2-Chloro-5-(chloromethyl)pyridineHCID 155479—
SolventEthanolHCID 702—
Product2-[(6-Chloropyridin-3-yl)methyl]-1H-isoindole-1,3(2H)-dioneHCID 1432471398.3%

Reaction Conditions

Temperature60 °C

Reaction Steps

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.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05214152
Source datasetuspto-grants-1993_05
ORD IDord-69b35144e0ef4190b4e807ad45adfdeb
Source noteuspto-grants-1993_05