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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 61827Generated: October 25, 2026

Water → 3-Chloro-8-(2-diethylaminoethoxy)-6,6-dimethyl-5,6-dihydro-benzo[b]carbazol-11-one

https://huagongshe.com/reaction/61827

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantCesium carbonateHCID 10796—
ReactantDiethylaminoethyl chlorideHCID 13364—
Reactant3-Chloro-8-hydroxy-6,6-dimethyl-5,6-dihydro-benzo[b]carbazol-11-oneHCID 66834241—
SolventDimethylformamideHCID 6228—
Product3-Chloro-8-(2-diethylaminoethoxy)-6,6-dimethyl-5,6-dihydro-benzo[b]carbazol-11-oneHCID 5458086688%

Reaction Conditions

Temperature80 °C

Reaction Steps

3-Chloro-8-hydroxy-6,6-dimethyl-5,6-dihydro-benzo[b]carbazol-11-one (Compound S2-1, 10 mg, 0.03207 mmol) was dissolved in DMF (0.1 mL), added with (2-chloroethyl)diethylamine (5.5 mg, 0.03207 mmol) and cesium carbonate (20.9 mg, 0.06414 mmol), and stirred at 80° C. for 2 hr. The reaction solution was added to water and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate. The residues obtained after concentration under reduced pressure were purified by NH silica gel column chromatography (ethyl acetate/hexane) to obtain the title compound (11.6 mg, 76%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09440922B2
Source datasetuspto-grants-2016_09
ORD IDord-4720445306624a5f8dc7d46fb430033d
Source noteuspto-grants-2016_09