Water → 6-(6,7-Dimethoxyquinolin-4-yloxy)naphthalen-1-amine

Participants

Reaction Steps

To a solution of 5-amino-2-naphthol (711 mg, 4.47 mmol) in NMP (3 ml), Cs2CO3 (4.37 g, 13.41 mmol) was added and the reaction was stirred at RT for 15 min. To the mixture, 4-chloro-6,7-dimethoxy-quinoline (500 mg, 2.23 mmol) was added and the vessel was sealed/clamped shut. The reaction was placed in the microwave and heated at 160° C. for 15 min, then 10 additional min with pre-stirring for 60 sec. The mixture was taken up into water and CH2Cl2, and filtered through Celite. The aqueous layer was extracted with CH2Cl2. The combined organic layers were washed with water, 1N NaOH, and brine, dried with Na2SO4, filtered and concentrated in vacuo. The 6-(6,7-dimethoxy-quinolin-4-yloxy)-naphthalen-1-ylamine was purified by column chromatography using 0-10% MeOH in CH2Cl2.

Provenance & Evidence