Stannous chloride dihydrate → methyl (2E)-3-(3,4-diaminophenyl)prop-2-enoate

참여 물질

반응 단계

To a solution of methyl (2E)-3-(4-amino-3-nitrophenyl)acrylate (from Step 2, 1 eq) in ethanol (0.2 M) was added tin(II) chloride dihydrate (5.75 eq). The reaction mixture was heated to reflux for 8 h. At this time the reaction was allowed to cool to RT, concentrated and diluted with EtOAc. A saturated aqueous solution of NaHCO3 was added slowly. The mixture was stirred for 20 min; the organic layer was washed with brine, dried over Na2SO4 filtered and evaporated in vacuo. The residue was purified by flash chromatography (SiO2; 70% EtOAc in PE) to afford the title compound (57%). 1H-NMR (400 MHz; DMSO-<d6, 300 K) δ 3.67 (s, 3H), 4.59 (s, 2H), 5.17 (s, 2H), 6.08 (d, J 15.6, 1H), 6.5 (d, J 8.0, 1H), 6.74 (d, J 7.6, 1H), 6.82 (s, 1H), 7.39 (d, J 15.6, 1H); MS (ES+) m/z 193 (M+H)+.

출처 및 근거