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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1724874Generated: October 31, 2026

1-(3-Chloropyridin-2-yl)ethanone → 5-Chloro-2-(3-chloropyridin-2-yl)-[1,8]naphthyridine

https://huagongshe.com/reaction/1724874

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1-(3-Chloropyridin-2-yl)ethanoneHCID 14644972—
ReactantPotassium tert-butoxideHCID 23665647—
Reactant2-Amino-4-chloropyridine-3-carbaldehydeHCID 46203541—
SolventTetrahydrofuranHCID 8028—
Product5-Chloro-2-(3-chloropyridin-2-yl)-[1,8]naphthyridineHCID 57561161—

Reaction Conditions

Temperature-20 °C

Reaction Steps

Dissolve 2-amino-4-chloronicotinaldehyde (312 mg, 2.0 mmol) and 2-acetyl-3-chloropyridine (310 mg, 2.0 mmol) in anhydrous THF (5.0 mL) and cool it to −20° C. under N2 atmosphere. Add in portion t-BuOK (448 mg, 4.0 mmol) to the reaction mixture and stir the mixture at 10° C. for 2 hours. Concentrate the reaction mixture under vacuum, dilute the residue with water (10 mL), filter the solid, wash the solid with water and dry under high vacuum to afford the title product as a yellow solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07488740B2
Source datasetuspto-grants-2009_02
ORD IDord-96e8cbfd6aa44777b0f8b9ec6aed11d6
Source noteuspto-grants-2009_02