7-(7-(benzyloxy)-6-methoxyquinolin-4-yloxy)-3,4-dihydro-2H-benzo[b][1,4]oxazine → 4-(3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yloxy)-6-methoxyquinolin-7-ol

Participants

Reaction Steps

Palladium, 10 wt % on activated carbon (0.050 g, 0.47 mmol) was added to a solution of 7-(7-(benzyloxy)-6-methoxyquinolin-4-yloxy)-3,4-dihydro-2H-benzo[b][1,4]oxazine (0.250 g, 0.60 mmol) in ethanol (10.0 mL). 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 4-(3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yloxy)-6-methoxyquinolin-7-ol (0.200 g, 102% yield) as a yellow-green solid. MS (MH+) 325.0; Calculated 324 for C18H16N2O4.

Provenance & Evidence