Sodium Dithionite → [3-Fluoro-4-methyl-2-(1-naphthalenyloxy)phenyl]amine

Participants

Reaction Steps

A solution of sodium hydrosulfite (25.8 g, 125 mmol) in water (120 mL) was added dropwise to a solution of 1-[(2-fluoro-3-methyl-6-nitrophenyl)oxy]naphthalene (6.2 g, 20.86 mmol) in THF (60 mL) at room temperature. The mixture was stirred at room temperature for 2 hrs. The reaction mixture was extracted with ethyl acetate (3×50 mL) and the combined organic layers were washed with brine, dried over sodium sulfate and concentrated. The residue was purified by flash chromatography (hexane:ethyl acetate) to give the title compound (3.34 g, 60%) as a light tan oil. 1H NMR (400 MHz, chloroform-d) δ ppm 8.44-8.52 (m, 1H), 7.80-7.90 (m, 1H), 7.45-7.61 (m, 3H), 7.19-7.32 (m, 1H), 6.86 (t, 1H), 6.64 (d, 1H), 6.53 (dd, 1H), 3.59 (br. s., 2H), 2.19 (s, 3H). ES MS m/z 268 (M+1).

Provenance & Evidence