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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1978005Generated: October 25, 2026

Dimethylformamide → 2-[3-(7-Methoxy-3,4-dihydronaphthalen-1-yl)propyl]isoindole-1,3-dione

https://huagongshe.com/reaction/1978005

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
Reactant4-(3-Bromopropyl)-6-methoxy-1,2-dihydronaphthaleneHCID 10423823—
ReactantPhthalimide potassium saltHCID 24194345—
SolventWaterHCID 962—
Product2-[3-(7-Methoxy-3,4-dihydronaphthalen-1-yl)propyl]isoindole-1,3-dioneHCID 2199645595.4%

Reaction Conditions

Temperature100 °C

Reaction Steps

A mixture of 4-(3-bromopropyl)-6-methoxy-1,2-dihydronaphthalene (10 g, 35.6 mmol), potassium phthalimide (7.9 g, 42.7 mmol) and DMF (50 ml ) was heated at 100° C. for 1 hour and then cooled. The mixture was diluted with water and the product was extracted with ethyl acetate. The extract was washed with brine and water, dried over anhydrous magnesium sulfate, and the solvent was removed in vacuo. The residue was purified by a silica gel column chromatography (ethyl acetate:hexane=2:8) to afford the titled compound (11.8 g, yield 95%, oil).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06235789B1
Source datasetuspto-grants-2001_05
ORD IDord-310b8a358cd847009b8e2b8c416d0584
Source noteuspto-grants-2001_05