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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1486925Generated: October 31, 2026

Diphenyl Ether → Ethyl 6-bromo-4-oxo-1,4-dihydroquinoline-3-carboxylate

https://huagongshe.com/reaction/1486925

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiphenyl EtherHCID 7583—
ReactantDiethyl 2-((4-bromophenylamino)methylene)malonateHCID 1591151—
SolventDiethyl EtherHCID 3283—
ProductEthyl 6-bromo-4-oxo-1,4-dihydroquinoline-3-carboxylateHCID 68982492.3%

Reaction Conditions

Temperature240 °C

Reaction Steps

Diphenyl ether (870 mL) was heated to 240° C. then diethyl 2-[[(4-bromophenyl)amino]methylidene]propanedioate (75 g, 219.18 mmol) added portionwise. The mixture was stirred at 240° C. for 60 minutes in a flask fitted with clean-stark apparatus. After cooling (25° C.) a crystallized solid was formed. The mixture was diluted with Et2O and the solid was collected by filtration, washed with Et2O and dried to afford the desired material (59.9 g) as a beige crystallized solid, which was used without purification or characterisation.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09428503B2
Source datasetuspto-grants-2016_08
ORD IDord-cbf4eb7d456645b095e94111a482a6ef
Source noteuspto-grants-2016_08