Diethyl (ethoxymethylene)malonate → HCID 21408193, Verbindung
Reaktionsgleichung
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]([CH3:12])[CH2:6][C:5]2=[O:13].C([O:16][CH:17]=[C:18]([C:24](OCC)=O)[C:19]([O:21][CH2:22][CH3:23])=[O:20])C>>[O:16]=[C:17]1[C:10]2=[CH:11][C:2]([F:1])=[CH:3][C:4]3=[C:9]2[N:8]([CH:7]([CH3:12])[CH2:6][C:5]3=[O:13])[CH:24]=[C:18]1[C:19]([O:21][CH2:22][CH3:23])=[O:20]Komponenten
3
Reaktionsbedingungen
- Temperatur
- 60 °C
Versuchsvorschrift
A stirred mixture of 12 g (0.067 mole) of 6-fluoro-2-methyl-4-oxo-1,2,3,4-tetrahydroquinoline from example 4 and 14.8 g (0.070 mole) of diethyl ethoxymethylenemalonate was heated gradually to 160° to 180° C. while removing the ethanol generated by distillation. After 0.5 hour the mixture was cooled to 60° C., and 30 g of polyphosphoric acid was added. This mixture was heated gradually to 150 to 160° C. and maintained at 155° to 160° C. for 5 to 10 minutes. Following cooling, water was added, and the mixture was kneaded to produce an orange powder which was separated by filtration. Recrystallization from a mixture of 500 ml of 95% ethanol and 100 ml of glacial acetic acid gave a yellow product, ethyl 6,7-dihydro-1,7-dioxo-9-fluoro-5-methyl-1H,5H-benzo[ij]-quinolizine-2-carboxylate, m.p. 262°-265° C.