Potassium Carbonate → 2-(2-Dimethylaminoethoxy)-4-nitroanisole

Participants

Reaction Steps

A stirred solution of 2-methoxy-5-nitrophenol (10 g, 0.059 mole) in 1,2-dimethoxyethane (80 ml) was treated with saturated aqueous potassium carbonate solution (32 ml) followed by 2-dimethylaminoethyl chloride hydrochloride (8.2 g, 0.057 mole) and heated under reflux for 17 hours. A further quantity of 2-dimethylaminoethyl chloride hydrochloride (4.0 g, 0.029 mole) was added and reflux was continued for 18 hours. The mixture was then concentrated in vacuo and the residue treated with 10% Na2 CO3 solution (100 ml) and extracted with ethyl acetate (2×100 ml). The combined extract was dried (Na2SO4) and concentrated in vacuo to afford the title compound as a yellow solid (11.8 g, 83%).

Provenance & Evidence