Triphenylphosphine → 2-(3-Nitrophenyl)ethan-1-amine

Participants

Reaction Steps

A mixture of 3-nitrophenethyl azide (0.9 g, 4.69 mmol), triphenyl phosphine (1.22 g, 4.66 mmol) and CH2Cl2 (80 mL) was stirred at room temperature for 3 days. Solvent was removed and the residue was taken up in EtOH (20 mL). The solution was heated to 70° C., added 2M NaOH aqueous solution (10 mL) and stirred at room temperature for 2 hrs. A 10% HCl aqueous solution (20 mL) was then added and refluxed for 2 hrs. After the mixture cool to room temperature, it was washed with benzene, basified with 5N NaOH to pH-12, extracted with ethyl acetate. The organic layer was dried over Na2SO4 and concentrated to give the product (0.63 g) as a yellow oil.

Provenance & Evidence