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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1784043Generated: October 30, 2026

Ethyl diazoacetate → Ethyl 3-(4-chlorophenyl)-2,4-dioxo-3-azabicyclo[3.1.0]hexane-6-carboxylate

https://huagongshe.com/reaction/1784043

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthyl diazoacetateHCID 12192—
ReactantMaleimide, N-(p-chlorophenyl)-HCID 15400—
SolventO-XyleneHCID 7237—
ProductEthyl 3-(4-chlorophenyl)-2,4-dioxo-3-azabicyclo[3.1.0]hexane-6-carboxylateHCID 312014635%

Reaction Steps

A solution of 19.4 g (93 mmol) of 1-(4-chloro-phenyl)-pyrrole-2,5-dione in 120 ml of xylene was treated with 19.4 ml (187 mmol) of ethyldiazoacetate and refluxed during 12 hrs. Evaporation of the solvent and chromatography on silica gel with toluene and then a gradient of toluene/AcOEt from 95:5 to 90:10 gave 9.5 g(35%) of the title compound. Off white solid. MS: 294 (M+H)+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07501413B2
Source datasetuspto-grants-2009_03
ORD IDord-01f24a38bb21480da8e3ab11a692e97a
Source noteuspto-grants-2009_03