[O:1]=[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([C:12]#[N:13])=[CH:7][CH:8]=2)[N:3]1[CH2:14][CH:15]=C.I([O-])(=O)(=O)=[O:18].[Na+]>O1CCOCC1.O.O=[Os](=O)(=O)=O>[O:1]=[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([C:12]#[N:13])=[CH:7][CH:8]=2)[N:3]1[CH2:14][CH:15]=[O:18]A solution of 2-oxo-1-(2-propen-1-yl)-1,2-dihydro-7-quinolinecarbonitrile (600 mg, 2.9 mmol) in 1,4-dioxane (30 ml) and water (20 ml) was cooled to 0° C. and treated with OsO4 (4% in water, 3 ml) and sodium periodate (1.4 g, 6.67 mmol). The reaction was warmed to rt; 0.6 g and then 3.7 g more of sodium periodate were added. After 4 h in total, the solvent was evaporated and residue partitioned between water and 20% methanol-DCM. The phases were separated and the organic phase was dried and evaporated to afford the desired compound (660 mg, 107%).
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