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

HRID 1588735Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1588735
[NH2:1][C:2]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=O.[C:17](OCC)(=[O:24])[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20].N1CCCCC1.C(OC(C)C)(C)C>>[Cl:16][C:13]1[CH:12]=[C:3]2[C:2](=[CH:15][CH:14]=1)[NH:1][C:17](=[O:24])[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:4]2[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Komponenten

5

Edukt 4

HCID 7761Diethyl MalonateHCID 7914Diisopropyl EtherHCID 8082PiperidineHCID 128702-Amino-5-chlorobenzophenone

Produkt 1

HCID 738703Ethyl 6-chloro-2-oxo-4-phenyl-1,2-dihydro-3-quinolinecarboxylateAusbeute 79,3 %

Reaktionsbedingungen

Temperatur
170 °C

Versuchsvorschrift

A mixture of 2-amino-5-chlorobenzophenone (6.93 g), diethyl malonate (7.2 g) and piperidine (0.3 ml) was heated at 170° C. for 4 hours. After cooling, isopropyl ether was added to the mixture to obtain crystals of ethyl 6-chloro-1,2-dihydro-2-oxo-4-phenyl-3-quinolinecarboxylate (7.77 g, 79.3%). The crystals was recrystallized from ethanol to give pale-yellowish needles. mp 223°-224° C.

Aufarbeitung

  1. temperatureAfter cooling

Quellen und Nachweise

ORD-Eintrag
ord-f231e14c85cd4fceadc86fc7a104ecc2
Quelldatensatz
uspto-grants-1993_06
Patentnummer
US05223513

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