Potassium Carbonate → HCID 58827300, compound

Participants

Reaction Steps

A mixture of 3-fluoro-4-nitrophenol (3.0 g, 19 mmol), 2-(dimethylamino)ethyl chloride hydrochloride (3.0 g, 21 mmol) and potassium carbonate (5.4 g, 39 mmol) in 2-butanone (75 mL) was heated to reflux for 20 hours. An additional portion of 2-(dimethylamino)ethyl chloride hydrochloride (2.0 g, 14 mmol) was added, and stirring at reflux proceeded for 24 hours. The mixture was cooled and evaporated under vacuum, and the residue was partitioned between ethyl acetate (100 mL) and water (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 into dilute aqueous HCl (3×75 mL). The combined aqueous extracts were washed with ethyl acetate (2×100 mL) and basified (NaOH), and the resulting mixture was extracted with ethyl acetate (3×100 mL). The combined extracts were washed with water (3×100 mL), dried (MgSO4), and evaporated, providing 2.9 g as a yellow oil, in 67% yield; 1H NMR (CDCl3) δ 2.34 (s, 6H), 2.76 (t, J=5.5 Hz, 2H), 4.13 (t, J=5.5 Hz, 2H), 6.72-6.81 (m, 2H), 8.09 (t, J=9.1 Hz, 1H).

Provenance & Evidence