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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 1497053Erstellt: 25. Oktober 2026

Diethyl Malonate → Ethyl 6-chloro-2-oxo-4-phenyl-1,2-dihydro-3-quinolinecarboxylate

https://huagongshe.com/reaction/1497053

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktDiethyl MalonateHCID 7761—
Edukt2-Amino-5-chlorobenzophenoneHCID 12870—
Edukt1,8-Diazabicyclo(5.4.0)undec-7-eneHCID 81184—
ProduktEthyl 6-chloro-2-oxo-4-phenyl-1,2-dihydro-3-quinolinecarboxylateHCID 73870349,5%

Reaktionsbedingungen

Temperatur185 °C

Reaktionsschritte

To a mixture of (2-amino-5-chloro-phenyl)-phenyl-methanone (5 g, 21.58 mmol) and malonic acid diethyl ester (4.565 ml, 30.21 mmol) was added DBU (0.45 ml, 3.02 mmol) under nitrogen and the mixture was stirred at 180-190° C. for 16 h. After cooling, the crude residue was purified by flash column chromatography (100-200 mesh silica, eluting with 50% ethyl acetate in hexane) to afford pure 6-chloro-2-oxo-4-phenyl-1,2-dihydro-quinoline-3-carboxylic acid ethyl ester (3.5 g, 49%) as off white solid. LC-MS: 328 (M+H)+.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS09199938B2
Quelldatensatzuspto-grants-2015_12
ORD IDord-90f5325a094f469d8076bf140a76a38e
Quellennotizuspto-grants-2015_12