Sodium Hydroxide → 6-bromo-4'-aminoflavone

Participants

Reaction Steps

Tin(II) chloride (275 mg, 1.45 mmol) was slowly added to an ethanol solution (7 ml) that contained compound 4 (100 mg, 0.289 mmol), while stirring. The obtained mixture was heated to reflux for 1 hour. After completion of the reaction, a 1 N sodium hydroxide aqueous solution (50 ml) was added to the reaction solution, and the obtained mixture was then extracted with 50 ml (25 ml×2) of ethyl acetate. The extract was dried over anhydrous sodium sulfate, and the solvent was then distilled away under reduced pressure, so as to obtain a product of interest, 6-bromo-4′-aminoflavone (compound 5) in the form of a yellow crystal. Yield: 77 mg (yield constant: 84.3%) 1H NMR (300 MHz, CDCl3) δ8.36 (s, 1H), 7.72-7.76 (m, 3H), 7.44 (d, J=9.0 Hz, 1H), 6.72 (d, J=8.7 Hz, 2H), 6.70 (s, 1H), 4.15 (s, 2H). MS m/z 317 (MH+).

Provenance & Evidence