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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 18128Generated: October 25, 2026

4-Chlorobutyryl chloride → 4-chloro-N-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}butanamide

https://huagongshe.com/reaction/18128

Reaction equation

Participants

RoleNameHCIDCharge
Reactant4-Chlorobutyryl chlorideHCID 78370—
Reactant11-amino-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dioneHCID 10065413—
ReactantDichloromethane methanolHCID 21226129—
SolventAcetonitrileHCID 6342—
Product4-chloro-N-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}butanamideHCID 1671783953%

Reaction Conditions

Temperature20 °C

Reaction Steps

A solution of 100 mg (0.30 mmole) of 11-amino-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione (obtained in example 3) in 4 mL of acetonitrile was stirred at 20° C. 68 μL of 4-chlorobutyryl chloride were added. The mixture was magnetically stirred at 20° C. during 3 hours. The solvent was then evaporated under reduced pressure and the residue was submitted to a flash chromatography on silica (eluent: CH2Cl2/methanol in a 97:3 volume ratio) to provide 70 mg (yield: 53%) of the desired product (formula below) as an orange powder

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07741337B2
Source datasetuspto-grants-2010_06
ORD IDord-d398ed68e3d64337be7c927a2afc5f77
Source noteuspto-grants-2010_06