Hydrochloric Acid → Isoquinolyl 4-methoxyphenyl ketone

HRID 604779

反応式

HRID 604779 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.BrCCBr.[Mg].[C:15]1([C:25]#N)[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][N:16]=1.Cl.[OH-:28].[Na+]>O1CCCC1.CO>[C:15]1([C:25]([C:2]2[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=2)=[O:28])[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[CH:17][N:16]=1

参加物

9

反応物 6

HCID 313Hydrochloric AcidHCID 77304-BromoanisoleHCID 78391,2-DibromoethaneHCID 14798Sodium HydroxideHCID 3060571-IsoquinolinecarbonitrileHCID 5462224Magnesium

生成物 1

HCID 693112Isoquinolyl 4-methoxyphenyl ketone

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

4-Bromoanisol (15.3 ml, 122 mmol) and a catalytic amount of 1,2-dibromoethane as an initiator were added to a mixed solution of magnesium (3059 mg, 125.8 mmol) and tetrahydrofuran (20 ml) under nitrogen atmosphere, and this reaction mixture was stirred while heating under reflux for 45 minutes. The mixture was cooled to 0° C., a solution of 1-isoquinolinecarbonitrile (10.78 g, 69.9 mmol) in tetrahydrofuran (30 ml) was added dropwise thereto, and this reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was cooled on ice, concentrated hydrochloric acid (24 ml) and methanol (120 ml) were added, and this mixture was heated under reflux for 1.5 hours. After cooling on ice, the mixture was adjusted to pH 8 by adding aqueous sodium hydroxide, extracted with ether, washed with saturated brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (15.87 g).

後処理

  1. temperaturewhile heating
  2. temperatureunder reflux for 45 minutes
  3. stirringthis reaction mixture was stirred at room temperature for 2 hours
  4. additionwere added
  5. temperaturethis mixture was heated
  6. temperatureunder reflux for 1.5 hours
  7. temperatureAfter cooling on ice
  8. extractionextracted with ether
  9. washwashed with saturated brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. concentrationconcentrated under reduced pressure
  12. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-9a130f8005c04dfaa58a55f87d6fd8f3
出典データセット
uspto-grants-2011_03
特許番号
US07910712B2

関連ノート

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