General procedure for the synthesis of (3-amino-5-methoxyphenyl)methanol from 3-amino-5-methoxybenzoic acid: lithium aluminum hydride (LiAlH4, 2.3 g, 0.06 mol) was added batchwise to an anhydrous tetrahydrofuran (THF, 100 mL) solution of 3-amino-5-methoxybenzoic acid (5 g, 0.03 mol) at 0 °C. The reaction mixture was stirred at 0 °C overnight and subsequently cooled to 0 °C and the reaction was quenched by slow addition of aqueous potassium hydroxide (20%, 5 mL) followed by addition of ethyl acetate (50 mL). The mixture was filtered through a diatomaceous earth pad and washed with ethyl acetate. The filtrate was dried with anhydrous sodium sulfate (Na2SO4), filtered and concentrated under reduced pressure. The crude product was purified by fast chromatography (eluent ratio tapered from 60:40 to 40:60, hexane:ethyl acetate) to afford (3-amino-5-methoxyphenyl)methanol (13) as a light yellow solid (2.75 g, 60% yield).1H NMR (400 MHz, CDCl3): δ 6.38 (s, 1H), 6.34 (s, 1H), and 6.31 (s, 1H), 4.39 (s, 2H), 3.79 (s, 3H), 3.77 (s, 2H).13C NMR (100MHz, CDCl3): δ160.61,147.49,143.13,105.90,102.04,99.87,64.98,54.78.
