2-Chloroquinoline → HCID 15177820, compound

Participants

Reaction Steps

3-(3-Pyridylmethyl)-4,6-chromandiol (5.0 g, 19.4 mmol; EP appln. 312,295) was dissolved in 100 ml dimethylformamide. 2-Chloroquinoline (3.17 g, 19.4 mmol) and then NaH (0.98 g of a 50% dispersion in oil, 20.4 mmol) were added and the mixture stirred at 90°-95° C. for 16 hours. The reaction mixture was cooled, quenched into 500 ml H2O, and extracted 4×400 ml ethyl acetate. The organic layers were combined, washed 3×400 ml H2O and 1×400 ml brine, dried (Na2 SO4), stripped to an oil (9.47 g) and chromatographed in silica gel gradiently eluted with 4-15% CH3OH in CH2Cl2 to yield 5.07 g of present title product as a white foam; IR (KBr) 3190, 1602, 1492 cm-1 ; MS 384 (M+).

Provenance & Evidence