Methyl iodide → 7-Fluoro-4-(methyloxy)-1-(2-propen-1-yl)-2(1H)-quinolinone

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Reaction Steps

To a solution of 7-fluoro-4-hydroxy-1-(2-propen-1-yl)-2(1H)-quinolinone (see Example 130(c) for a preparation) (1.0 g, 4.56 mmol) in DMF (50 ml) at 0° C. was added sodium hydride (0.20 g, 5.0 mmol, 60% in paraffin). To the resulting solution was added methyl iodide (0.3 ml, 4.8 mmol) and stirring continued at 0° C. for 1 h, then at ambient for 18 h. The mixture was evaporated and the residues separated between dichloromethane and water. The organics were isolated, dried and concentrated. Chromatography over silica (50 g SPE, eluting with dichloromethane) provided the title compound (0.386 g, 36%).

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