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

Participants

Reaction Conditions

Reaction Steps

SnCl2.2H2O (5.20 g, 23.0 mmol) was added to a stirred solution of (E/Z) 4-[1-(3,5-dimethoxy-phenyl)-propenyl]-1-methoxy-2-nitro-benzene (1.10 g, 3.2 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 a mixture of (E/Z) 5-[1-(3,5-dimethoxy-phenyl)-propenyl]-2-methoxy-phenylamine as an oil (0.64 g, 51% yield): 1H NMR (CDCl3) δ 1.70-1.78 (2d, J=7.0 Hz, 6H, 2CH3), 3.74-3.87 (4s+m, 22H, 6OCH3+2NH2), 6.02-6.10 (m, 2H, 2CH), 6.33-6.79 (m, 12H, Ar); 13C NMR (CDCl3) δ 15.60, 15.73, 55.30, 55.45, 55.52, 98.70, 98.92, 105.72, 107.99, 109.95, 109.99, 113.91, 116.77, 117.30, 120.32, 122.05, 123.83, 132.49, 135.56, 135.61, 142.09, 142.33, 142.50, 145.66, 146.32, 146.56, 160.36, 160.51; Anal. Calcd for C18H21NO3: C, 72.22; H, 7.07; N, 4.68. Found: C, 71.94; H, 7.37; N, 4.54.

Provenance & Evidence