3,4-Bis(benzyloxy)aniline synthesis
- Product Name:3,4-Bis(benzyloxy)aniline
- CAS Number:18002-44-3
- Molecular formula:C20H19NO2
- Molecular Weight:305.37
28387-13-5
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Yield:18002-44-3 73%
Reaction Conditions:
with acetic acid;zinc in dichloromethane at 0; for 0.166667 h;Inert atmosphere;
Steps:
3-(Benzyloxy)-4-methoxyaniline (S3a)
General procedure: Reduction was carried out using modifiedprocedure reported by Zhou et al.4 Under an argon atmosphere, activated zinc powder5(20.2 g, 309 mmol) was added portionwise to a solution of S2a (10.0 g, 38.6 mmol) inDCM (390 mL) at room temperature. After cooling to 0 °C, AcOH (57.9 mL) was addeddropwise to the suspension. After stirring for 10 min at 0 °C, the suspension was allowed to warm toroom temperature and then passed through a pad of Celite. The filtrate was evaporated and the residuewas diluted with DCM. The mixture was washed with saturated aqueous NaHCO3 and brine, driedover Na2SO4, and evaporated. The residue was purified by column chromatography over silica gel60N (DCM-ethyl acetate = 100:1) to give S3a as a dark purple solid (7.86 g, 89%). 1H NMR(500 MHz, CDCl3): d 3.33 (br s, 2H), 3.81 (s, 3H), 5.11 (s, 2H), 6.24 (dd, J = 2.6 and 8.4 Hz, 1H),6.32 (d, J = 2.6 Hz, 1H), 6.74 (d, J = 8.4 Hz, 1H), 7.27-7.32 (m, 1H), 7.34-7.38 (m, 2H), 7.41-7.45(m, 2H). 13C NMR (126 MHz, CDCl3): d 57.0, 70.9, 103.3, 107.2, 114.1, 127.2, 127.8, 128.5, 137.3,140.6, 142.8, 149.2. HRFABMS m/z calcd for C14H16NO2 [(M+H)+]: 230.1181, found 230.1181.These physical and spectroscopic data are in good agreement with those previously reported.2
References:
Fukuda, Tsutomu;Anzai, Mizuho;Nakahara, Akane;Yamashita, Kentaro;Matsukura, Kazuaki;Ishibashi, Fumito;Oku, Yusuke;Nishiya, Naoyuki;Uehara, Yoshimasa;Iwao, Masatomo [Bioorganic and Medicinal Chemistry,2021,vol. 34,art. no. 116039] Location in patent:supporting information
3316-09-4
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