Ammonium Chloride → HCID 67040794, compound

Participants

Reaction Steps

A suspension of 4-(4-tert-butoxycarbonylamino-phenoxy)-3-nitro-benzoic acid methyl ester (18.0 g, 46 mmol), Fe powder (13.5 g, 232 mmol) and NH4Cl (12.4 g, 232 mmol) in aqueous EtOH [prepared from EtOH (180 mL) and H2O (180 mL)] was gradually heated to reflux and refluxed for 1.5 hours. The reaction mixture was filtrated through celite pad and the filtrate was evaporated. The aqueous residue was portioned between AcOEt and 5% NaHCO3 and then filtered through celite pad. The organic layer was separated, washed H2O and brine, dried over MgSO4 and evaporated to give pale brown oil, which was diluted with i-Pr2O (100 mL) and stirred at room temperature for 1 hour. The resulting crystal was collected by filtration, washed with i-Pr2O, and dried at 40° C. overnight under reduced pressure to give the title compound as colorless crystal (10.5 g, 63%).

Provenance & Evidence