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, is 1H), 4.40 (t, 2H), 3.75 (t, 4H), 3.01 (t, 2H), 2.66 (t, 4H). MS: 303 (M+1).

Provenance & Evidence