Bromide ion → HCID 53881747, compound

Participants

Reaction Steps

3.19 Grams of the mixture of 5-allyl-1-cinnamyl-3,4-dihydro-6-hydroxy-2(1H)-quinolinone and 7-allyl-1-cinnamyl-3,4-dihydro-6-hydroxy-2(1H)-quinolinone obtained in Example 13 was dissolved in 100 ml of methanol containing 1 g of potassium hydroxide. Under stirring, 2 g of cinnamy bromide was added thereto at room temperature, then stirred at room temperature for 1 hour, further stirred at 60° C. for 4 hours. After the reaction was finished, the reaction mixture was concentrated to a half volume under reduced pressure, 100 ml of water was added and stirred vigorously, then extracted with 200 ml of ethyl acetate. The extract was washed with water and an aqueous solution saturated with sodium chloride and dried with anhydrous magnesium sulfate. The magnesium sulfate was removed by filtration, the filtrate was concentrated to dryness. The residue was subjected to treatment by means of a silica gel flush column chromatography by using a mixed solvent of ethyl acetate: n-hexane as the eluent. The second eluted portion was collected and concentrated and crystallized from diethyl ether-n-hexane, there was obtained 1.8 g (41.4%) of 5-allyl-1-cinnamyl-6-cinnamyloxy-3,4-dihydro-2(1H)-quinolinone. Colorless granular crystals (recrystallized from diethyl ether-n-hexane). Melting point: 66°-68° C.

Provenance & Evidence