Propan-2-one--water (1/1) → 1-(4-Fluorophenyl)-6-formyl-4-oxo-1,4-dihydroquinoline-3-carboxamide

Participants

Reaction Steps

To a solution of compound F (385 mg, 1.25 mmol) in 3:1 acetone/water (8 mL) was added N-oxide-4-methylmorpholine (220 mg, 1.87 mmol) and osmium tetroxide (254 μL, 0.025 mmol). After the reaction stirred for one hour, sodium periodate (294 mg, 1.37 mmol) was added. After another two hours, the reaction was diluted with EtOAc and washed well with a 10% NaS2O3 solution. The organic layer was dried (MgSO4), filtered and concentrated in vacuo to give 365 mg (94%) of the title compound that was used without further purification. ES-MS [M+1]+: 311.2.

Provenance & Evidence