Ammonium Chloride → (4-Amino-3-benzylamino-phenyl)-carbamic acid tert-butyl ester

Participants

Reaction Steps

To a solution of (3-benzylamino-4-nitro-phenyl)-carbamic acid tert-butyl ester E-1.5′ (5.000 g; 15 mmol) in ethanol (50.000 g) is added a solution of ammonium chloride (3.932 g, 73 mmol) in water (10 ml). The reaction mixture is then stirred at 70° C. for 20 min Iron powder (4.077 g; 73 mmol) is then added portionwise and the reaction is stirred for 4 h at reflux. The reaction mixture is filtered and washed with hot ethanol. The filtrate is concentrated under reduced pressure. Water is added and the mixture is extracted with 10% MeOH in DCM. The combined organic layer is dried over Na2SO4 and concentrated under reduced pressure. The product is used in the next step without further purification.

Provenance & Evidence