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

HRID 577472

반응식

HRID 577472 반응식
[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

참가 물질

6

반응물 3

HCID 31297Methanesulfonyl chlorideHCID 11062313Boron, trifluoro(methanol)-, (T-4)-HCID 89350921HCID 89350921, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 24193Titanium Tetrachloride촉매HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-5ea636e0cd3f4155a2a87985ff4141c0
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040515B2

연결된 노트

불러오는 중…