Sodium Hydroxide → 2-(2-Benzyloxyphenyl)-6-morpholinoquinolin-4-one

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Reaction Steps

To a solution of 92 (1.2 g, 2.7 mmol) in 1,4 dioxane (150 ml) was added NaOH (0.9 g, 21.4 mmol). The mixture was refluxed for 5 h, concentrated and added 10% NH4Cl (100 ml). The precipitate was collected and washed with H2O and acetone. The crude product was purified by column chromatography (silica gel, CHCl3:MeOH=25:1) to give 113 as yellow solid (1.3 g, 3.2 mmol). Yield: 65.4%; mp 281-283° C.; MS (EI, 70 eV): m/z 412.4 (M+); 1H-NMR (DMSO-d6. 200 MHz): δ 3.15 (m, 4H), 3.77 (m, 4H), 5.12 (s, 2H), 6.30 (s, 1H), 7.36-7.50 (m, 11H), 7.66 (d, J=9.2 Hz, 1H), 11.57 (s, 1H); Anal. Calcd for C26H24N2O3; C, 75.71; H, 5.86; N, 6.79.

Provenance & Evidence