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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1504188Generated: November 4, 2026

Hydrochloric Acid → HCID 131731813, compound

https://huagongshe.com/reaction/1504188

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrochloric AcidHCID 313—
Reactant2-BromopyridineHCID 7973—
Reactant1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 636044—
ReactantSodium n-butylateHCID 23669364—
Reactant1-methyl-6-[5-(2-pyridin-3-ylethylamino)pentyloxy]-1H-quinolin-2-oneHCID 66960104—
Catalystpalladium(II) acetateHCID 167845—
SolventEthanolHCID 702—
SolventWaterHCID 962—
SolventTolueneHCID 1140—
ProductHCID 131731813HCID 131731813—

Reaction Conditions

Temperature80 °C

Reaction Steps

1-methyl-6-[5-(2-pyridin-3-ylethylamino)pentyloxy]-1H-quinolin-2-one(182 mg), 2-bromopyridine(0.060 ml), palladium acetate (II) (11.2 mg), xantphos (32 mg), and sodium-butoxide(68 mg) were added to toluene(2 ml). The mixture was heated at 80° C. for 10 hours under nitrogen atmosphere. The reaction liquid was cooled to room temperature. Water 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). The purified product was condensed under reduced pressure. A 1N-hydrogen chloride in ethanol solution(0.58 ml) was added to a ethanol solution (5 ml) of the residue, and the liquid was stirred at room temperature, and concentrated under reduced pressure. Ethanol and diethyl ether were added to the residue. The precipitated insoluble matter was separated, washed with diethyl ether, and dried to give the title compound(72 mg) as a yellow powder.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09212187B2
Source datasetuspto-grants-2015_12
ORD IDord-a586be18bc31416eb82d596a2c72b606
Source noteuspto-grants-2015_12