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

HRID 1957536ノート

反応式

HRID 1957536 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-109cae1271d045e58684438be1860755
出典データセット
uspto-grants-1998_07
特許番号
US05786367

反応ノート

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