2-(Chloromethyl)quinoline → HCID 18971781, compound

Participants

Reaction Steps

NaH (63 mg, 1.58 mmol, 1.0 eq, 60% oil dispersion) was added to a mixture of (0.500 g, 1.58 mmol, 1.0 eq) 5-[3-(bicyclo[2.2.1]hept-2-yloxy)4-methoxyphenyl]tetra-hydro-2(1H)-pyrimidinone and (0.279 g, 1.58 mmol, 1.0 eq) 2-chloromethylquinoline in 12 ml of anhydrous dimethylformamide. After stirring for 18 hours at room temperature, the reaction mixture was diluted with 250 ml of H2O and extracted with ethyl acetate. The ethyl acetate extract was washed once with H2O, once with brine, dried over Na2SO4, and concentrated in vacuo. The residue was chromatographed on a silica gel column, eluting with 21/2% CH3OH-CH2Cl2 to yield 50 mg of a solid, which was recrystallized from ethyl acetate-hexane to afford 45 mg, 5%, of a white crystalline solid. M.P.: 135°-136° C.

Provenance & Evidence