ChemicalBook CAS DataBase List (E)-4-(3, 5-Dimethoxystyryl) aniline

(E)-4-(3, 5-Dimethoxystyryl) aniline synthesis

13synthesis methods

Product Name:(E)-4-(3, 5-Dimethoxystyryl) aniline
CAS Number:586410-15-3
Molecular formula:C16H17NO2
Molecular Weight:255.31

586410-18-6 Synthesis

1,3-DiMethoxy-5-[2-(4-nitro-phenyl)-vinyl]-benzene

586410-18-6
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586410-15-3
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Yield:586410-15-3 89%

Reaction Conditions:

with tin(II) chloride dihdyrate in ethyl acetate; for 5 h;Reflux;Inert atmosphere;

Steps:

4.1.3 General procedure for the preparation of (E)-4-(3,5-dimethoxystyryl)aniline (5)

Compound 4 (7mmol, 2.00g) dissolved in ethyl acetate (15mL) was added with tin (II) chloride dihydrate (35mmol, 7.90g) and the mixture was refluxed for 5h. The reaction was then terminated by the addition of saturated sodium bicarbonate solution. The resulting mixture was extracted with ethyl acetate. The organic layer was washed with water and brine and then dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography to give the target compound. Yield 89%, pale yellow solid; ¹H NMR (500MHz, CDCl₃) δ 7.33 (d, J=8.4Hz, 2H), 7.00 (d, J=16.2Hz, 1H), 6.85 (d, J=16.2Hz, 1H), 6.67 (d, J=8.4Hz, 2H), 6.64 (d, J=2.0Hz, 2H), 6.36 (t, J=2.1Hz,1H), 6.36 (s, 6H), 3.75 (br.s, 2H); ESI-MS m/z: 256.1 [M+H]⁺.

References:

Li, Shanshan;Zhang, Wenda;Yang, Yanwei;Ma, Ting;Guo, Jianpeng;Wang, Shanshan;Yu, Wenying;Kong, Lingyi [European Journal of Medicinal Chemistry,2016,vol. 124,p. 1006 - 1018]