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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 1740636Erstellt: 26. Oktober 2026

Ethyl bromoacetate → 1-[2-(2-Oxo-1,2-dihydroquinolin-1-yl)-4-pyridyl]-2-ethoxycarbonylmethoxymethyl-3-hydroxymethyl-6,7-dimethoxynaphthalene

https://huagongshe.com/reaction/1740636

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktEthyl bromoacetateHCID 7748—
EduktEthyl AcetateHCID 8857—
EduktSodium hydrideHCID 24758—
Edukt1-[2-(2-Oxo-1,2-dihydroquinolin-1-yl)-4-pyridyl]-2,3-bis(hydroxymethyl)-6,7-dimethoxynaphthaleneHCID 9912467—
LösungsmittelWaterHCID 962—
LösungsmittelDimethylformamideHCID 6228—
Produkt1-[2-(2-Oxo-1,2-dihydroquinolin-1-yl)-4-pyridyl]-2-ethoxycarbonylmethoxymethyl-3-hydroxymethyl-6,7-dimethoxynaphthaleneHCID 22007427—
Produkt1-[2-(2-Oxo-1,2-dihydroquinolin-1-yl)-4-pyridyl]-2-hydroxymethyl-3-ethoxycarbonylmethoxymethyl-6,7-dimethoxynaphthaleneHCID 22007435—

Reaktionsschritte

To a solution of 1-[2-(2-oxo-1,2-dihydroquinolin-1-yl)-4-pyridyl]-2,3-bis(hydroxymethyl)-6,7-dimethoxynaphthalene (468 mg) in dimethylformamide (5 ml) is added sodium hydride (60 mg), and the mixture is stirred for 30 minutes. The mixture is cooled with ice, and thereto is added dropwise ethyl bromoacetate (0.17 ml), and the mixture is stirred overnight. To the residue are added ethyl acetate and water, and the ethyl acetate layer is separated, washed, dried and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (solvent; chloroform:acetone=5:1) to give 1-[2-(2-oxo-1,2-dihydroquinolin-1-yl)-4-pyridyl]-2-ethoxycarbonylmethoxymethyl-3-hydroxymethyl-6,7-dimethoxynaphthalene (70 mg, Example 96) and 1-[2-(2-oxo-1,2-dihydroquinolin-1-yl)-4-pyridyl]-2-hydroxymethyl-3-ethoxycarbonylmethoxymethyl-6,7-dimethoxynaphthalene (120 mg, Example 97), which are listed in Table 8.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS05969140
Quelldatensatzuspto-grants-1999_10
ORD IDord-b0db2ded5c13455e8148e687abcbf721
Quellennotizuspto-grants-1999_10