Potassium Carbonate → 4-(2-((4-Nitronaphthalen-1-yl)oxy)ethyl)morpholine

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-nitro-1-hydroxynaphthalene (10 g, 52.8 mmol), 4-(2-chloroethyl)-morpholine hydrochloride (13.77 g, 74.0 mmol), sodium hydroxide (3.0 g, 74.0 mmol), potassium carbonate (17.53 g, 126.8 mmol) and 1-methyl-2-pyrrolidinone (400 ml) is heated to 90°-100° C. for 2-3 hours. The mixture is cooled to 40° C. and water (300 ml) added. The mixture is then cooled to 0° C. and held for 4 hours. The product is precipitated and collected by filtration, washed with water, cyclohexane and dried under vacuum to yield 4-[2-(4-nitro-naphthalen-1-yloxy)-ethyl]-morpholine (14.73 g, 92.6%). 1H NMR 300 MHz (CDCl3) 8.80(d, 1H), 8.38(t, 2H), 7.75(t, 1H), 7.63(t, 1H), 6.84(d, 1H), 4.40(t, 2H), 3.75(t, 4H), 3.01(t, 2H), 2.66(t, 4H). MS: 303 (M+1).

Provenance & Evidence