Diethyl (formylamino)(8-quinolinylmethyl)malonate → ethyl 2,3,6,7-tetrahydro-3-oxo-2-(formylamino)-1H,5H-benzo(ij)quinolizine-2-carboxylate
Reaktionsgleichung
[CH:1]([NH:3][C:4]([CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]2[C:25]=1[N:24]=[CH:23][CH:22]=[CH:21]2)([C:10](OCC)=[O:11])[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[O:2].[H][H]>C(O)(=O)C.[Pt]=O>[O:11]=[C:10]1[C:4]([NH:3][CH:1]=[O:2])([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:15][C:16]2=[CH:17][CH:18]=[CH:19][C:20]3=[C:25]2[N:24]1[CH2:23][CH2:22][CH2:21]3Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
A mixture of diethyl (formylamino)(8-quinolinylmethyl)malonate (9.2 g, 26.7 mmol) and platinum oxide (0.7 g) in glacial acetic acid (150 mL) was hydrogenated (50 lb initial pressure) for 15 minutes (hydrogen uptake ca. 2 equiv). The mixture was filtered through celite and the solvent removed under reduced pressure. The product was partitioned between ethyl acetate and sodium hydroxide solution. The ethyl acetate phase was washed with water, the ethyl acetate was evaporated, and the product was crystallized from ether to give 7.8 g (97%) of ethyl 2,3,6,7-tetrahydro-3-oxo-2-(formylamino)- 1H,5H-benzo(ij)quinolizine-2-carboxylate, mp 103°-106° C. Anal. Calc'd for C16H18N2O4 : C, 63.56; H, 6.00; N, 9.27. Found: C, 63.51; H, 6.09; N, 9.18.
Aufarbeitung
- customfor 15 minutes
- filtrationThe mixture was filtered through celite
- customthe solvent removed under reduced pressure
- customThe product was partitioned between ethyl acetate and sodium hydroxide solution
- washThe ethyl acetate phase was washed with water
- customthe ethyl acetate was evaporated
- customthe product was crystallized from ether
Quellen und Nachweise
- ORD-Eintrag
- ord-7eff329947704dc0a297d998208b65f6
- Quelldatensatz
- uspto-grants-1995_07
- Patentnummer
- US05436240
Notizen zur Reaktion
Wird geladen…