Sodium hydride → HCID 53943986, compound

Participants

Reaction Steps

2.4 Grams of the mixture of 6-allyl-7-allyloxy-3,4-dihydro-2(1H)-quinolinone and 6-allyl-7-allyloxy-3,4-dihydro-2(1H)-quinolinone as the reaction intermediate obtained in Example 14 was dissolved in 20 ml of dimethylformamide, then 0.6 g of 60% oily sodium hydride and 2.5 g of cinnamyl bromide were added thereto at room temperature and reacted similarly as in Reference example 7, there was obtained yellow oily product by treating thus obtained reaction mixture. Said oily product was dissolved in 50 ml of tetralin and stirred at 200° to 230° C. for 3 hours. After cooling, the reaction mixture was subjected to purification by passing through a silica gel column, there was obtained 1.2 g (33.4%) of 6,8-diallyl-1-cinnamyl-3,4-dihydro-7-hydroxy-2(1H)-quinolinone. Pale yellow flake crystals (recrystallized from isopropyl ether). Melting point: 132°-138° C.

Provenance & Evidence