Diethyl Ether → HCID 59327640, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of N′-(2-(4-chlorophenyl)-2-methylpropanoyl)-3-oxobutanehydrazide (1.77 g, 6.0 mmol) in ethanol (15 ml) was added 2-amino acetophenone (0.61 ml, 5.0 mmol) followed by ytterbium triflate (310 mg, 0.5 mmol). The mixture was heated at 70° C. for 12 hours, cooled to room temperature, and the ethanol was removed under reduced pressure. The crude residue was dissolved in ethyl acetate, poured into a separatory funnel, and washed with water (2×), saturated sodium bicarbonate, and brine. The organic phase was separated, and solvent removed under reduced pressure, to provide a viscous oil, which solidified upon the addition of ethyl ether. The solid was filtered off and washed with diethyl ether, to provide N′-(2-(4-chlorophenyl)-2-methylpropanoyl)-2,4-dimethylquinoline-3-carbohydrazide (1.8 g, 91%) as a light yellow powder. TLC Rf=0.44 using 100% ethyl acetate eluent on a glass backed silica gel plate.

Provenance & Evidence