Reaktionsgleichung
Br[C:2]1[CH:3]=[C:4]2[CH2:16][CH2:15][CH:14]([CH2:17][C:18](OC)=[O:19])[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23.C[N:23](C=O)C.[C:27]([OH:30])(=O)C.[H][H]>C1COCC1.[Pd]>[CH3:27][O:30][NH:23][C:18]([CH2:17][CH:14]1[N:6]2[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]3[CH:11]=[CH:2][CH:3]=[C:4]([C:5]=32)[CH2:16][CH2:15]1)=[O:19]Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
9-Bromo-5-methoxycarbonylmethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]quinoxaline-2,3-dione (1.15 g, 3.26 mmol) in a mixture of THF (5 mL), DMF (10 mL), and acetic acid (8 mL) was hydrogenated over palladium on carbon (300 mg) under atmospheric pressure of hydrogen at room temperature for 5 h. The mixture was passed through celite and concentrated. The residue was purified by silica gel column chromatography with ethyl acetate to give 700 mg of 5-methoxycarbamoylmethyl-6,7-dihydro-1H, 5H-pyrido[1,2,3-de]-quinoxaline-2,3-dione (79%): 227°~229° C. (dec); 1H NMR (270 MHz, DMSO-d6) δ12.00 (bs, 1H), 6.97~7.12 (m, 2H), 5.06~5.16 (m, 1H), 3.63 (s, 3H), 2.97 (ddd, 1H, J=17.1, 13.5, 4.5 Hz), 2.79 (dm, 1H, J=17.1 Hz), 2.54~2.69 (m, 2H), 2.12 (dm, 1H, J=13.5 Hz), 1.82~2.00 (m, 1H).
Aufarbeitung
- concentrationconcentrated
- customThe residue was purified by silica gel column chromatography with ethyl acetate
Quellen und Nachweise
- ORD-Eintrag
- ord-8391c1c25c6f4d9e88f09b3990991ec4
- Quelldatensatz
- uspto-grants-1997_04
- Patentnummer
- US05616586
Verknüpfte Notizen
Wird geladen…