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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1770135Generated: October 26, 2026

Water → 6-[3-(N-methyl-N-benzylamino)-2-hydroxypropoxy]carbostyril

https://huagongshe.com/reaction/1770135

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantSodium hydrideHCID 24758—
Reactant2,6-DihydroxyquinolineHCID 177065—
Reactant1-chloro-2-hydroxy-3-(N-methyl-N-benzylamino)propaneHCID 14719871—
SolventDimethylformamideHCID 6228—
Product6-[3-(N-methyl-N-benzylamino)-2-hydroxypropoxy]carbostyrilHCID 1035977522.6%

Reaction Steps

To a solution of 6-hydroxycarbostyril (1.6 g) and sodium hydride (50% oily) (1 g) in dimethylformamide (30 ml), 1-chloro-2-hydroxy-3-(N-methyl-N-benzylamino)propane (2.2 g) is added dropwise at room temperature. After the addition, the mixture is heated with stirring at 70°-80° C. for 3 hours. The reaction mixture is poured into water and extracted with chloroform, and the extract is dried over magnesium sulfate. Chloroform is distilled off and the resulting residue is purified by silica gel column chromatography (solvent; methanol:chloroform=1:100-1:25) and recrystallized from ethanol to give 6-[3-(N-methyl-N-benzylamino)-2-hydroxypropoxy]carbostyril (0.76 g), as white powder, m.p. 129°-132° C.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05385914
Source datasetuspto-grants-1995_01
ORD IDord-440b0e3c66944ba3ad85353db6b347cd
Source noteuspto-grants-1995_01