Stannous chloride dihydrate → 3-Aminocinnamic acid ethyl ester

Participants

Reaction Steps

Ethyl 3-nitrocinnamate (1) (2.0 g, 9.04 mmol) was reduced using method A, except that SnCl2.2H2O (10.2 g, 45.20 mmol) in EtOH (20 mL) was used and after the reaction the solvent was concentrated in vacuo, Rochelle's salt and saturated NaHCO3 (1:1, 80 mL) were added, and the aqueous basified with 1N NaOH. The aqueous was extracted with EtOAc (3×40 mL), washed with Rochelle's salt/saturated NaHCO3 solution (2×40 mL), dried (MgSO4) and the solvent was concentrated in vacuo to give the title compound. Yield: 1.77 g, >100%; LC/MS tr 0.89 min; MS (ES+) m/z 192 (M+H)

Provenance & Evidence