Ammonium Chloride → 3-Amino-4-(4-hydroxy-phenylsulfanyl)-benzoic acid methyl ester

Participants

Reaction Steps

A suspension of 4-(4-hydroxy-phenylsulfanyl)-3-nitro-benzoic acid methyl ester (5.60 g, 18 mmol), Fe powder (5.34 g, 92 mmol) and NH4Cl (4.91 g, 92 mmol) in aqueous EtOH [prepared from EtOH (50 mL) and H2O (50 mL)] was gradually heated to reflux and refluxed for 45 minutes. The reaction mixture was diluted with AcOEt (50 mL) and filtered through celite pad. The filtrate was evaporated and the aqueous residue was portioned between AcOEt and 10% NaHCO3. The organic layer was separated, washed with H2O and brine, dried over MgSO4 and evaporated to give pale yellow solid. The resulting solid was washed with i-Pr2O and dried at 40° C. for 3 days under reduced pressure to give the title compound as slightly yellow crystal (4.50 g, 90% by 2 steps).

Provenance & Evidence