Ammonium Chloride → (4-Amino-3-methoxy-benzyl)-benzyl-carbamic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of benzyl-(3-methoxy-4-nitro-benzyl)-carbamic acid tert-butyl ester (1.2 g, 3.22 mmol) in methanol (24 mL) was added a saturated aqueous solution of NH4Cl (24 mL) and zinc powder (1.05 g 16.11 mmol). The reaction was heated to 60° C. for 2 hours then the reaction mass was cooled to room temperature and filtered through celite. The solvents were removed under reduced pressure then the residue was partitioned between EtOAc (24 mL) and water (24 mL). The separated aqueous layer was extracted with EtOAc (12 ml), and then the combined organic extracts were washed with water (24 mL), brine (24 mL), dried (Na2SO4) and concentrated under reduced pressure to give the title compound (0.94 g, 85%).

Provenance & Evidence