Nitrogen → 2-(2-Dimethylaminoethoxy)-4-nitroanisole

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-methoxy-5-nitro-phenol (10 g), (2-chloro-ethyl)-dimethyl-amine hydrochloride (9.37 g) in dimethylformamide (150 mL) was added NaH (2.98 g) slowly under N2 and at room temperature. The mixture was then stirred at 140° C. heating with an oil bath for 5 hours. The reaction was concentrated to dryness, dissolved in 2 M HCl (200 mL) and washed with ethyl acetate (2×100 mL). The aqueous layer was basified with K2CO3, extracted with dichloromethane (3×200 mL) and ethyl acetate (2×100 mL), dried over Na2SO4, filtered, concentrated to give [2-(2-Methoxy-5-nitro-phenoxy)-ethyl]-dimethylamine (9.17 g, 65% yield). LCMS (m/z) M+H: 241.1.

Provenance & Evidence