Stannous chloride dihydrate → Methyl 3-aminocinnamate
Reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-])=O)[CH:7]=1.O.O.Cl[Sn]Cl>C(O)C>[CH3:1][O:2][C:3](=[O:15])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH2:12])[CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
A mixture of 3-(3-nitro-phenyl)-acrylic acid methyl ester (22) (10.0 g, 48 mmol) and SnCl2.2H2O (54 g, 240 mmol) in anhydrous ethanol (200 ml) was heated at 80° C. for 1 hour. The reaction mixture was allowed to cool to room temperature, then the solvent was partially evaporated by vacuum rotary evaporator (up to ca. ½ volume). The residue was poured in ice water, neutralised (pH˜7) with saturated Na2CO3 and the resulting mixture was extracted with ethyl acetate. The organic extract was washed with saturated NaCl and dried (Na2SO4). The extract was filtrated through a small amount of silica gel and evaporated to give pure title compound in a form of white crystals (8.5 g, 99%). 1H NMR (CDCl3, HMDSO), δ: 3.69 (2H, br s), 3.79 (3H, s); 6.39 (1H, d, J=16.0 Hz); 6.61–7.03 (3H, m); 7.18 (1H, t, J=7.6 Hz); 7.62 (1H, d, J=16.0 Hz).