4-Nitrophenol → N,N-dimethyl-3-(4-nitrophenoxy)propan-1-amine

Participants

Reaction Steps

A stirred solution of diethyl azodicarboxylate (4.6 ml, 0.029 mole) and triphenylphosphine (7.60 g, 0.029 mole) in dry TBF (100 ml) was cooled to 0° C. 3-(Dimethylamino)propanol (3.43 ml, 0.029 mole) was added, followed by 4-nitrophenol (4.0 g, 0.029 mole) and the reaction mixture was stirred for 18 h at room temperature. The solvent was removed in vacuo, and the residue partitioned between 5N HCl and ethyl acetate. The aqueous layer was basified with 10% NaOH solution and extracted into ethyl acetate, dried (MgSO4) and evaporated in vacuo to leave the title compound as a yellow oil (3.2 g, 50%).

Provenance & Evidence