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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1846992Generated: October 30, 2026

Itaconic acid → 5-Oxo-1-(3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl)pyrrolidin-3-carboxylic acid

https://huagongshe.com/reaction/1846992

Reaction equation

Participants

RoleNameHCIDCharge
ReactantItaconic acidHCID 811—
Reactant6-amino-3,4-dihydro-2H-1,4-benzoxazin-3-oneHCID 2763681—
SolventWaterHCID 962—
Product5-Oxo-1-(3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-yl)pyrrolidin-3-carboxylic acidHCID 8672492496%

Reaction Steps

A mixture of 6-amino-2H-1,4-benzoxazin-3(4H)-one (4.93 g, 30.0 mmol), itaconic acid (4.06 g, 31.2 mmol) and water (80 ml) was heated under reflux overnight. The reaction solution was cooled, and the insoluble material was collected by filtration and washed with water and diethyl ether. The filtrate was dried at 50° C. under reduced pressure to yield 7.92 g (96%) of the title compound in the form of a brownish solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08952010B2
Source datasetuspto-grants-2015_02
ORD IDord-11322bb82aaf49388cc2a6261866a1e3
Source noteuspto-grants-2015_02