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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 476512Generated: October 29, 2026

Pyridine → 2-(7-fluoro-4-propargyl-2H-1,4-benzoxazin-3(4H)-on-6-yl)-4,5,6,7-tetrahydro-1,2,3-benzotriazole-1-oxide

https://huagongshe.com/reaction/476512

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPyridineHCID 1049—
Reactant2-[2-(7-fluoro-4-propargyl-2H-1,4-benzoxazin-3(4H)-on-6-yl)hydrazino]cyclohexanone oximeHCID 86743537—
CatalystCopper SulfateHCID 24462—
SolventWaterHCID 962—
SolventTetrahydrofuranHCID 8028—
Product2-(7-fluoro-4-propargyl-2H-1,4-benzoxazin-3(4H)-on-6-yl)-4,5,6,7-tetrahydro-1,2,3-benzotriazole-1-oxideHCID 14517954—

Reaction Conditions

Temperature80 °C

Reaction Steps

To a solution of 2-[2-(7-fluoro-4-propargyl-2H-1,4-benzoxazin-3(4H)-on-6-yl)hydrazino]cyclohexanone oxime (0.4 g) in tetrahydrofuran (6 ml), 15% aqueous pyridine (7 g) was added, and a solution of copper sulfate (0.7 g) in water (1.5 ml) was added thereto, followed by heating at 80° C. for 2 hours. The reaction mixture was allowed to cool, combined with water and extracted with ethyl acetate. The organic layer was washed with 10% aqueous copper sulfate solution, dried and concentrated. The residue was purified by silica gel column chromatography using ethyl acetate as an eluent to give Compound No. 1 (0.2 g). m.p., 186°-187° C.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04885024
Source datasetuspto-grants-1989_12
ORD IDord-542bd86611a448529b031e8b1afeaf4c
Source noteuspto-grants-1989_12