4-Nitrophenol → N,N-dimethyl-2-(4-nitrophenoxy)ethanamine

Participants

Reaction Steps

A mixture of 4-nitrophenol (3.5 g, 25 mmol), 2-(dimethylamino)ethyl chloride hydrochloride (3.6 g, 25 mmol), and potassium carbonate (13.2 g, 125 mmol) in acetone (100 mL) was heated to reflux for 30 hours. The solvent was removed under vacuum. The residue was partitioned between water (150 mL) and ethyl acetate (150 mL), and the aqueous phase was extracted with ethyl acetate (100 mL). The combined organic layers were washed with water (3×150 mL) and extracted with dilute aqueous HCl (2×125 mL). These extracts were washed with CH2Cl2 (2×150 mL), made basic (NaOH) and extracted into ethyl acetate (3×75 mL). These organic extracts were washed with water (3×75 mL), dried (MgSO4), and evaporated, providing 3.0 g as a pale yellow solid, in 57% yield; 1H NMR (CDCl3) δ 2.35 (s, 6H), 2.76 (t, J=5.6 Hz, 2H), 4.15 (t, J=5.6 Hz, 2H), 6.96-7.00 (m, 2H), 8.17-8.22 (m, 2H).

Provenance & Evidence