sodium tetrahydroborate; tin(ll) chloride in methanol; ethanol 1 h; Heating;

1: HCl, Fe, H2 / H2O 2: NaOH, NaHCO3 / H2O / 8 h / 15 - 25 °C View Scheme

1: propionic acid With iodine; triethylamine; phosphorous acid trimethyl ester in dichloromethane 0.166667 h; Cooling with iceInert atmosphere; 2: 3-nitro-aniline in dichloromethane T=20°C; 4 h; Inert atmosphereCooling with ice;

Product distribution;

Product distribution;