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

HRID 1588737Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1588737
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:16][CH3:17])=[C:6]([CH:15]=1)[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=O.[C:18](OCC)(=[O:25])[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21].N1CCCCC1.C(OC(C)C)(C)C>>[Cl:1][C:2]1[CH:15]=[C:6]2[C:5](=[CH:4][CH:3]=1)[N:16]([CH3:17])[C:18](=[O:25])[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:7]2[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Komponenten

5

Edukt 4

HCID 7761Diethyl MalonateHCID 7914Diisopropyl EtherHCID 8082PiperidineHCID 139252-(Methylamino)-5-chlorobenzophenone

Produkt 1

HCID 10405076Ethyl 6-chloro-1,2-dihydro-1-methyl-2-oxo-4-phenyl-3-quinolinecarboxylateAusbeute 73,1 %

Versuchsvorschrift

A mixture of 5-chloro-2-methylaminobenzophenone (1.23 g), diethyl malonate (1.6 g) and piperidine (0.1 ml) was heated for 3 hours at 170°-180° C. After cooling, the mixture was treated with isopropyl ether to give crystals, which were recrystallized from ethanol to afford ethyl 6-chloro-1,2-dihydro-1-methyl-2-oxo-4-phenyl-3-quinolinecarboxylate (1.25 g, 73.1%). mp 124°-125° C. The product was identical with the compound obtained in Reference Example 12.

Aufarbeitung

  1. temperaturewas heated for 3 hours at 170°-180° C
  2. temperatureAfter cooling
  3. customto give crystals, which
  4. customwere recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-54191ea06d1f4bf3b784a8d02b8317e6
Quelldatensatz
uspto-grants-1993_06
Patentnummer
US05223513

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