O-[(4-methoxyphenyl)methyl]Hydroxylamine

Synthesis

General procedure for the synthesis of 4-methoxybenzyloxyamine from N-(4-methoxybenzyloxy)phthalimide: To a solution of ethanol (7 mL) containing N-(4-methoxybenzyloxy)phthalimide (0.7 mmol, 236 mg) was added hydrazine hydrate (0.77 mmol, 0.04 mL). The reaction mixture was stirred at 80 °C for 1 hour. After completion of the reaction (monitored by thin layer chromatography), the resulting mixture was concentrated under vacuum. The residue was dissolved in ether, filtered and washed twice with ether. The filtrate was concentrated under vacuum to give 4-methoxybenzyloxyamine as a colorless oil (138 mg, 95% yield).1H NMR (400 MHz, CDCl3) δ 7.31 (d, J = 8.0 Hz, 2H), 6.92 (d, J = 7.9 Hz, 2H), 5.36 (s, 2H), 4.63 (s, 2H), 4.16 (t, J = 4.7 Hz, 2H), 3.60 (t, J = 4.8 Hz, 2H).13C NMR (100 MHz, CDCl3) δ 158.1, 130.2, 130.1, 114.6, 77.5, 67.0, 50.1.

References

[1] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 10, p. 2434 - 2437
[2] Journal of Polymer Science, Part A: Polymer Chemistry, 2010, vol. 48, # 16, p. 3553 - 3563
[3] Molecules, 2013, vol. 18, # 4, p. 3872 - 3893
[4] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 3, p. 607 - 610
[5] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 19, p. 3155 - 3159