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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 69024Generated: October 30, 2026

Hydrochloric Acid → 1-methyl-6-{3-[N-(1-oxo-1,2-dihydroisoquinolin-4-yl)-N-(pyridin-4-ylmethyl)amino]propoxy}-1H-quinolin-2-one

https://huagongshe.com/reaction/69024

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrochloric AcidHCID 313—
ReactantSodium HydroxideHCID 14798—
Reactant6-{3-[N-(1-Methoxyisoquinolin-4-yl)-N-(pyridin-4-ylmethyl)amino]propoxy}-1-methyl-1H-quinolin-2-oneHCID 86762692—
SolventEthanolHCID 702—
Product1-methyl-6-{3-[N-(1-oxo-1,2-dihydroisoquinolin-4-yl)-N-(pyridin-4-ylmethyl)amino]propoxy}-1H-quinolin-2-oneHCID 8676269138.6%

Reaction Conditions

Temperature75 °C

Reaction Steps

6-{3-[N-(1-Methoxyisoquinolin-4-yl)-N-(pyridin-4-ylmethyl)amino]propoxy}-1-methyl-1H-quinolin-2-one (55 mg) was added to a 1N-hydrogen chloride in ethanol solution (5 ml), and stirred at 75° C. for 2 hours. The reaction mixture was cooled to room temperature. 1N-Sodium hydroxide aqueous solution (5 ml) was added to the reaction mixture, followed by extraction with dichloromethane. The organic layer was dried over anhydrous sodium sulfate. The filtrate was condensed under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:methanol=10:0→4:1). The purified product was condensed under reduced pressure to give the title compound (20.6 mg) as a colorless oil.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08822453B2
Source datasetuspto-grants-2014_09
ORD IDord-9994e1a92f7944fbaf70aabf1aaddbbe
Source noteuspto-grants-2014_09