3-Nitrophenol → 1-(2-Dimethylaminoethoxy)-3-nitrobenzene

Participants

Reaction Conditions

Reaction Steps

3-Nitro phenol (1 g, 7.19 mmol) was added to a solution of potassium hydroxide (1.6 g, 28.76 mmol) in anhydrous DMSO (6 ml) at room temperature. After 30 min, (2-chloro-ethyl)-dimethyl-amine hydrochloride (1.03 g, 7.19 mmol) was added and the reaction mixture was heated at 80-90° C. for 12 hr. The reaction mixture was cooled to room temperature and diluted with ice water. The product was extracted with toluene and the organic layer was washed with 5% sodium hydroxide solution, then brine and dried. Evaporation under reduced pressure gave dimethyl-[2-(3-nitro-phenoxy)-ethyl]-amine (600 mg, 40%) as oil.

Provenance & Evidence