Sodium Hydroxide → 5-[1-(3,5-Dimethoxy-phenyl)-vinyl]-2-methoxy-phenylamine

Participants

Reaction Conditions

Reaction Steps

SnCl2.2H2O (4.41 g, 19.54 mmol) was added to a stirred suspension of 3-(3,5-dimethoxy-phenyl)-3-(4-methoxy-3-nitro-phenyl)-acrylonitrile (1.12 g, 3.55 mmol) in ethanol (200 proof, 20 mL) and ethyl acetate (10 mL). The reaction mixture was heated at 70° C. for 1 h. The solution was cooled down to room temperature, poured into ice water (100 mL), and basified with 10 N NaOH (20 mL) to pH ˜12. The aqueous layer was extracted with ethyl acetate (5×35 mL). The combined organic layers were washed with water (60 mL), brine (50 mL) and dried (MgSO4). Removal of solvent and chromatography (Silica Gel) gave 5-[1-(3,5-dimethoxy-phenyl)-vinyl]-2-methoxy-phenylamine as a solid (0.64 g, 63% yield): mp, 93-95° C.; 1H NMR (CDCl3) δ 3.77-3.87 (2s+m, 11H, 3OCH3+NH2), 5.31-5.37 (dd, J=1.2, 13.1 Hz, 2H, CH2), 6.43-6.73 (m, 6H, Ar); 13C NMR (CDCl3) δ 55.36, 55.53, 99.77, 106.69, 109.92, 112.80, 1.14.92, 118.62, 134.13, 135.63, 144.19, 147.21, 149.86, 160.40; Anal. Calcd for C17H19NO3: C, 71.56; H, 6.71; N, 4.91. Found: C, 71.31; H, 6.76; N, 4.92.

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