51307-59-6

3717-21-3

51307-59-6

To a methanolic solution of (E)-4-methoxybenzaldehyde oxime (compound D) (1.0 mL containing 77.8 mg, 0.52 mmol) was added sodium cyanoborohydride (NaBH3CN, 22.7 mg, 0.36 mmol) at room temperature. Subsequently, the pH of the reaction mixture was adjusted to 3 by slow addition of 2 M HCl-MeOH solution and stirred continuously for 3 h at room temperature. Upon completion of the reaction, the reaction mixture was alkalized to basic by dropwise addition of 15% NaOH aqueous solution. After saturation with the addition of sodium chloride, the mixture was extracted with ethyl acetate. The organic layers were combined, dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by fast column chromatography (eluent: chloroform/methanol = 1:0 → 10:1) to afford N-(4-methoxybenzyl)hydroxylamine (73.5 mg, 92% yield) as white crystals.1H NMR (CDCl3) δ: 7.25 (d, J = 8.6 Hz, 2H), 6.87 (d, J = 8.6 Hz, 2H), 4.73 (brs. 2H), 3.97 (s, 2H), 3.80 (s, 3H).