Hydrogen Peroxide → HCID 22735319, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the crude 6-trifluoromethoxy-quinoline of Step A (obtained from 50 mmol of 4-trifluoromethoxy aniline) in glacial acetic acid (54 mL) is added dropwise 30% hydrogen peroxide (8 mL). The mixture is heated at 82° C. under nitrogen for 16 hours, cooled, carefully basified with concentrated ammonium hydroxide and extracted with ethyl acetate. The extracts are washed with brine, dried over anhydrous magnesium sulfate and evaporated to dryness. The residue is twice azeotroped with benzene, and then flash chromatographed on silica gel Merck-60 using dichloromethane followed by a gradient of methanol (0.5–2%) in dichloromethane to provide the title compound as a pale brown oil that solidifies upon standing. The pale brown crystals (4.8 g) melt at 68–70° C.

Provenance & Evidence