4,7-Dichloroquinoline → 2-[2-(7-Chloroquinolin-4-ylamino)ethoxy]ethanol

Participants

Reaction Steps

A mixture of 4,7-dichloroquinoline (5.0 g, 25.0 mmol) and of 2-(2-aminoethoxy)ethanol (10.51 g, 100.0 mmol) is heated at 135° C. for 5 h, with magnetic stirring. After cooling, the reaction medium is taken up in 200 ml of diethyl ether and the stirring is maintained overnight at ambient temperature. The solid residue formed is isolated, and then dissolved in a mixture of 500 ml of dichloromethane/triethylamine (9/1, v/v) and filtered through sintered glass containing a bed of silica (SiO2 60 AAC 70-200 μm). The product is then eluted from the silica with ethanol (2 l). The ethanolic phases are combined and evaporated. 50 ml of dichloromethane are added to the residue and the organic phase is washed with twice 50 ml of water. The organic phase is recovered, dried over Na2SO4, and then evaporated in a rotary evaporator. After drying under vacuum, the compound 21 is obtained in the form of a beige powder: 5.03 g (yield=75%).

Provenance & Evidence