4-Bromoanisole → 6-allyloxy-3,4-dihydro-1-(4-methoxyphenyl)-2(1H)-quinolinone

HRID 1957536노트

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HRID 1957536 반응식
[CH2:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10](=[O:15])[CH2:9][CH2:8]2)[CH:2]=[CH2:3].[H-].[Na+].Br[C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1>CN(C)C=O>[CH2:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)[C:10](=[O:15])[CH2:9][CH2:8]2)[CH:2]=[CH2:3]

참가 물질

5

반응물 3

HCID 77304-BromoanisoleHCID 24758Sodium hydrideHCID 190680326-(allyloxy)-3,4-dihydroquinolin-2(1H)-one

생성물 1

HCID 190679946-allyloxy-3,4-dihydro-1-(4-methoxyphenyl)-2(1H)-quinolinone수율 42%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
120 °C

실험 절차

2 Grams of 6-allyloxy-3,4-dihydro-2(1H)-quinolinone was dissolved in 50 ml of dimethyl-formamide, then 0.5 g of 60% oily sodium hydride and 5 ml of p-bromoanisole were added thereto by the procedures similar to those employed in Reference example 7, further 4 g of cuprous chloride was added, and stirred at 120° C. for 24 hours. The inorganic materials were removed by filtration, and the filtrate was concentrated under reduced pressure. Thus obtained residual product was subjected to extraction with 200 ml of methylene chloride, the extract was washed with water and an aqueous solution saturated with sodium chloride. Then the extract was concentrated and subjected to purification by passing through a silica gel column, there was obtained 1.3 g (42%) of 6-allyloxy-3,4-dihydro-1-(4-methoxyphenyl)-2(1H)-quinolinone.

후처리

  1. additionwas added
  2. customThe inorganic materials were removed by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. extractionThus obtained residual product was subjected to extraction with 200 ml of methylene chloride
  5. washthe extract was washed with water
  6. concentrationThen the extract was concentrated
  7. customsubjected to purification

출처 및 근거

ORD 기록
ord-109cae1271d045e58684438be1860755
출처 데이터셋
uspto-grants-1998_07
특허 번호
US05786367

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