Ethyl Acetate → 1-(2-Amino-4-(benzyloxy)-5-methoxyphenyl)ethanone

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Reaction Steps

A mixture of 1-(4-(benzyloxy)-5-methoxy-2-nitrophenyl)ethanone (3.6 g, 12 mmol), iron powder (4.5 g) and ammonium formate (5.5 g) in toluene (50 mL) and water (50 mL) was heated at reflux temp. for 2 days with stirring. To this mixture was added EtOAc (100 mL), stirred for 20 minutes, the solid was filtered through a celite bed and washed with EtOAc (150 mL). The EtOAc layer was separated from the filtrate solution, washed with water (2×100 mL), dried over MgSO4 and concentrated in vacuo to afford the product (2.80 g, 86%) as a beige-colored solid. 1H NMR (CDCl3) δ 7.41-7.30 (m, 5H), 7.13 (s, 1H), 6.15 (br s, 2H), 6.10 (s, 1H), 5.13 (s, 2H), 3.84 (s, 3H), 2.51 (s, 3H).

Provenance & Evidence