Hydrochloric Acid → (4-Butylphenyl)(isoquinolin-1-yl)methanone

HRID 604771

反応式

HRID 604771 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH3:11])=[CH:4][CH:3]=1.[Mg].BrCCBr.[C:17]1([C:27]#N)[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][N:18]=1.Cl.[OH-:30].[Na+]>CO.O1CCCC1>[CH2:8]([C:5]1[CH:6]=[CH:7][C:2]([C:27]([C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=[CH:19][N:18]=2)=[O:30])=[CH:3][CH:4]=1)[CH2:9][CH2:10][CH3:11]

参加物

9

反応物 6

HCID 313Hydrochloric AcidHCID 78391,2-DibromoethaneHCID 14798Sodium HydroxideHCID 3060571-IsoquinolinecarbonitrileHCID 5210591-Bromo-4-butylbenzeneHCID 5462224Magnesium

生成物 1

HCID 17851496(4-Butylphenyl)(isoquinolin-1-yl)methanone

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

Under a nitrogen atmosphere, 1-bromo-4-butylbenzene (2.29 ml, 13.0 mmol) was added to a mixed solution of magnesium (338 mg, 13.9 mmol) and tetrahydrofuran (6.5 ml), and as an initiator, catalytic amount of 1,2-dibromoethane was added, and this was stirred under reflux for 10 minutes. The solution was cooled to 0° C., a tetrahydrofuran solution of 1-isoquinolinecarbonitrile (1.0 g, 6.49 mmol) was added, and was stirred for another 1 hour at room temperature, and at 70° C. for 3 hours. Subsequently, the solution was cooled again to 0° C., concentrated hydrochloric acid (2.56 ml) and methanol (11 ml) were added, and then refluxed for 2 hours. The concentrated residue was dissolved in 5 N sodium hydroxide and toluene, and was filtered through celite. The toluene layer of the filtrate was divided, washed with water, dried over magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography to give 1.72 g of the title compound.

後処理

  1. temperatureunder reflux for 10 minutes
  2. stirringwas stirred for another 1 hour at room temperature
  3. temperatureSubsequently, the solution was cooled again to 0° C.
  4. temperaturerefluxed for 2 hours
  5. filtrationtoluene, and was filtered through celite
  6. washwashed with water
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-8e519db212f541efa528f6f993d192d9
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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