Methanesulfonyl chloride → 7-Methoxy-3,4-dihydroisoquinolin-1(2H)-one

HRID 577472

反応式

HRID 577472 の反応式
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8]/[C:9]/2=[N:12]\OS(C)(=O)=O)=[CH:5][CH:4]=1.B(F)(F)F.CO.CS(Cl)(=O)=[O:26]>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][NH:12][C:9]2=[O:26])=[CH:5][CH:4]=1

参加物

6

反応物 3

HCID 31297Methanesulfonyl chlorideHCID 11062313Boron, trifluoro(methanol)-, (T-4)-HCID 89350921HCID 89350921、化合物

生成物 1

HCID 135216727-Methoxy-3,4-dihydroisoquinolin-1(2H)-one収率 117.1%

試薬・触媒・溶媒 2

HCID 24193Titanium Tetrachloride触媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a stirred suspension of (1E)-6-methoxy-N-[(methylsulfonyl)oxy]-2,3-dihydro-1H-inden-1-imine (1b, 27 g, 106 mmol), BF3/MeOH (14% in MeOH, 16.8 g, 170 mmol) and TiCl4 (32.3 g, 170 mmol) in dry DCM (200 mL) was added MsCl (20.9 g, 183 mmol) dropwise at 0° C. After the addition, the resulting solution was stirred at room temperature for 14 hours. To the reaction mixture was added DCM (200 mL) and the solution was washed with saturated NaHCO3 to pH ˜7. The organic layer was washed with brine (150 mL), dried over Na2SO4, and concentrated under vacuum. The residue was purified by column chromatography (DCM/MeOH) to give 7-methoxy-3,4-dihydroisoquinolin-1(2H)-one (1c, 22 g, 100%) as a gray solid.

後処理

  1. additionAfter the addition
  2. washthe solution was washed with saturated NaHCO3 to pH ˜7
  3. washThe organic layer was washed with brine (150 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by column chromatography (DCM/MeOH)

出典と根拠

ORDレコード
ord-5ea636e0cd3f4155a2a87985ff4141c0
出典データセット
uspto-grants-2015_05
特許番号
US09040515B2

関連ノート

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