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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 497582Generated: October 25, 2026

Maleic Anhydride → 4-[(6-chloro-1H-indazol-3-yl)amino]-4-oxo-2-butenoic acid

https://huagongshe.com/reaction/497582

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMaleic AnhydrideHCID 7923—
Reactant6-chloro-1H-indazol-3-amineHCID 85628—
SolventO-XyleneHCID 7237—
Product4-[(6-chloro-1H-indazol-3-yl)amino]-4-oxo-2-butenoic acidHCID 6704279163.1%

Reaction Conditions

Temperature145 °C

Reaction Steps

585 mg of preground maleic anhydride are added to 1 g of 6-chloro-1H-indazole-3-amine in 30 cm3 of ortho-xylene. The reaction medium is refluxed at 145° C. for ten minutes and then cooled in a water bath. The insoluble material is filtered off and washed successively with 2×25 cm3 of ethyl acetate and then with 2×25 cm3 of diisopropyl ether. The solid is then dried under reduced pressure (90 Pa; 50° C.) to give 1 g of 4-[(6-chloro-1H-indazol-3-yl)amino]-4-oxo-2-butenoic acid (Z form) in the form of yellow crystals melting at 230° C.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06949579B2
Source datasetuspto-grants-2005_09
ORD IDord-753497c62f804f97b114565b58b850c0
Source noteuspto-grants-2005_09