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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2383833Generated: November 1, 2026

Methanol → 5-[3-(4-Methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-1,2-dihydro-indazol-3-one

https://huagongshe.com/reaction/2383833

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethanolHCID 887—
ReactantHydrazine hydrate (1:1)HCID 24654—
Reactant2-Fluoro-5-[3-(4-methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-benzoic acid methyl esterHCID 68785967—
SolventChloroformHCID 6212—
SolventDichloromethaneHCID 6344—
Product5-[3-(4-Methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-1,2-dihydro-indazol-3-oneHCID 5963623337.6%

Reaction Conditions

Temperature120 °C

Reaction Steps

2-Fluoro-5-[3-(4-methyl-pyridin-3-yl)-2-oxo-imidazolidin-1-yl]-benzoic acid methyl ester (I-117a: 510 mg, 1.55 mmol) and hydrazine hydrate were taken in a reaction flask and the flask was heated to 120° C. for 18 hours with stirring. The reaction was monitored by TLC (10% MeOH in CHCl3). The reaction mixture was partitioned between ice water and ethylacetate. The aqueous layer was concentrated to afford the solid residue which was dissolved in 1:1 DCM: MeOH and filtered. The filtrate was concentrated and purified by column chromatography on silica gel (10-15% MeOH in CHCl3). The residue was washed with DCM and dried to afford 180 mg of the product (37.6% yield).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08263635B2
Source datasetuspto-grants-2012_09
ORD IDord-a896e41a87b14f7f8e207c3579853e95
Source noteuspto-grants-2012_09