Sodium hydride → HCID 22987165, compound

Participants

Reaction Conditions

Reaction Steps

A solution under argon of 4-(2-ethyl-1,3-dioxan-2-yl)-1,2-dihydro-2-pyridinone (obtained according to 4.e, 11 g, 52 mmol) in anhydrous tetrahydrofuran (370 ml) is treated at 0° C. with sodium hydride (80% in mineral oil, 1.68 g, 56 mmol). The resulting mixture is maintained under agitation at 0° C. for 15 min then treated with 3-bromomethyl-2-chloroquinoline (obtained according to 4.b, 13.4 g, 52 mmol) and the resulting mixture is maintained under agitation at ambient temperature for 24 hours. The reaction medium is then poured into an aqueous solution saturated in ammonium chloride (400 ml), the phases are separated, and the aqueous phase aqueuse is extracted with dichloromethane. The combined organic phases are washed with saturated aqueous sodium chloride, dried over magnesium sulphate and concentrated under reduced pressure. The residue taken up in diethyl ether forms a precipitate which is collected by filtration and dried in order to produce 13.8 g (69%) of a white solid.

Provenance & Evidence