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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1634727Generated: October 31, 2026

Potassium Carbonate → 8-(Benzyloxy)-5-[(2S)oxiranylmethoxy]-3,4-dihydro-2(1H)-quinolinone

https://huagongshe.com/reaction/1634727

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPotassium CarbonateHCID 11430—
ReactantBenzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl esterHCID 146490—
Reactant8-(Benzyloxy)-5-hydroxy-3,4-dihydroquinolin-2(1H)-oneHCID 12751737—
SolventMethyl Ethyl KetoneHCID 6569—
Product8-(Benzyloxy)-5-[(2S)oxiranylmethoxy]-3,4-dihydro-2(1H)-quinolinoneHCID 2338134482.1%

Reaction Steps

A mixture of 8-(benzyloxy)-5-hydroxy-3,4-dihydro-2(1H)-quinolinone (0.20 g, 0.743 mmol), (S)-(+)-glycidyl 3-nitrobenzenesulfonate (0.193 g, 0.743 mmol) and potassium carbonate (0.113 g, 0.817 mmol) in 2-butanone (10 mL) was heated at reflux for 16 hours. The solvent was removed in vacuo and the residue purified by flash chromatography (chloroform-methanol, 50:1) to yield the title compound (0.210 g, 0.61 mmol).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06506901B2
Source datasetuspto-grants-2003_01
ORD IDord-60d95559de3842d6aeac341fa2e20646
Source noteuspto-grants-2003_01