Water → HCID 57720099, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-dimethylamino-6-iodo-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid (2.77 g, 7.73 mol) in MeCN (70 ml), CuI (0.15 g, 0.773 mol) and TEA (37.5 ml, 270 mol) were added and stirred for 20 minutes and then warmed up to 50° C. To the reaction mixture propargyl alcohol (1.08 ml, 2.4 mmol) and Pd(PPh3)2Cl2 (0.27 g, 0.39 mol) were added and stirred at 50° C. for 3 hours. Then water (130 ml) and diisopropyl-ether (100 ml) were added, the pH was adjusted to 12, the layers were separated and H2O layer extracted with diisopropyl-ether (2×50 ml). To the water layer EtOH (14 ml) and charcoal were added, heated to the reflux temperature, and filtered through celite. Then the pH of H2O solution was adjusted to 6, extracted with DCM (200 ml), combined organic layers were evaporated to obtain the crude product. Precipitation from DCM-hexane afforded the title product (1.25 g, 56%).

Provenance & Evidence