Dichloromethane → (7-Fluoro-2-oxo-1(2H)-quinolinyl)acetaldehyde

Participants

Reaction Steps

A solution of 7-fluoro-1-(2-propen-1-yl)-2(1H)-quinolinone (0.909 g, 4.48 mmol) in 1,4-dioxane (50 ml) and water (30 ml) at 0° C. was treated with sodium periodate (2.20 g, 10.30 mmol) and OsO4 (4% in water, 5 ml). The reaction was warmed to rt and stirred at rt for 1 h before an extra 30 ml of water was added, after another 1 h more sodium periodate (2.20 g, 10.30 mmol) was added and after a further 2 h more sodium periodate (4.20 g, 19.70 mmol) was added. The reaction was then stirred at rt for 0.5 h before evaporation, treatment with water and extraction with DCM (×3). The combined organics were dried and evaporated to give the desired product (0.50 g, 88%). This material contained approximately 10% of the isomeric (5-fluoro-2-oxo-1(2H)-quinolinyl)acetaldehyde.

Provenance & Evidence