7-(6-(benzyloxy)-7-methoxyquinolin-4-yloxy)-3,4-dihydro-2H-benzo[b][1,4]oxazine → 4-(3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yloxy)-7-methoxyquinolin-6-ol
Reaktionsgleichung
C([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[O:19][CH3:20])[N:15]=[CH:14][CH:13]=[C:12]2[O:21][C:22]1[CH:23]=[CH:24][C:25]2[NH:30][CH2:29][CH2:28][O:27][C:26]=2[CH:31]=1)C1C=CC=CC=1>C(O)C.[Pd]>[O:27]1[CH2:28][CH2:29][NH:30][C:25]2[CH:24]=[CH:23][C:22]([O:21][C:12]3[C:11]4[C:16](=[CH:17][C:18]([O:19][CH3:20])=[C:9]([OH:8])[CH:10]=4)[N:15]=[CH:14][CH:13]=3)=[CH:31][C:26]1=2Komponenten
4
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
Palladium, 10 wt % on activated carbon (0.100 g, 0.940 mmol) was added to a solution of 7-(6-(benzyloxy)-7-methoxyquinolin-4-yloxy)-3,4-dihydro-2H-benzo[b][1,4]oxazine (1.156 g, 2.79 mmol) in ethanol (20.0 mL). The system was evacuated and purged with hydrogen (g) three times and then stirred under a H2 (g) atmosphere for 18 h. Additional palladium, 10 wt % on activated carbon (0.100 g, 0.940 mmol) was added to the reaction mixture. The system was evacuated and purged with hydrogen (g) three times and then stirred under a H2 (g) atmosphere for 20 h. The reaction mixture was filtered through a pad of Celite and concentrated to afford an orange brown solid. This material was purified via column chromatography on silica gel (RediSep 40 g column, gradient elution with 0-100% (90:10:1, dichloromethane/methanol/ammonium hydroxide)-dichloromethane) to afford 4-(3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yloxy)-7-methoxyquinolin-6-ol (0.733 g, 81.0% yield) as a yellow solid. MS (MH+) 325.0; Calculated 324 for C18H16N2O4.