2-(Dimethylamino)ethanol → [2-(3-Isopropoxy-4-nitrophenoxy)ethyl]dimethylamine

Participants

Reaction Conditions

Reaction Steps

N,N-Dimethylethanolamine (1.6 g, 18 mmol) was added to a mixture of powdered KOH (1.0 g, 18 mmol) and Aliquat 336 (0.72 g, 1.8 mmol), and the resulting mixture was stirred for 5 minutes at 80° C. Then 4-fluoro-2-isopropoxy-1-nitrobenzene (3.0 g, 15 mmol) was added, and stirring proceeded at this temperature for 30 minutes. The mixture was cooled and partitioned between methylene chloride (100 mL) and dilute aqueous HCl (100 mL), and the organic layer was extracted with dilute aqueous HCl (2×100 mL). The combined aqueous phases were washed with methylene chloride (3×150 mL), basified (3N NaOH), and extracted with methylene chloride (3×100 mL). The combined organic extracts were washed with water (3×100 mL), dried (MgSO4), and evaporated, providing 2.2 g as a yellow oil, in 55% yield; 1H NMR (CDCl3) δ 1.40 (d, J=6.1 Hz, 6H), 2.34 (s, 6H), 2.74 (t, J=5.6 Hz, 2H), 4.10 (t, J=5.6 Hz, 2H), 4.61 (septet, J=6.1 Hz, 1H), 6.48 (dd, J=9.1 Hz, J=2.5 Hz, 1H), 6.57 (d, J=2.5 Hz, 1H), 7.91 (d, J=9.1 Hz, 1H).

Provenance & Evidence