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

HRID 577472

Reaction equation

HRID 577472 reaction equation
[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

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-5ea636e0cd3f4155a2a87985ff4141c0
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Linked notes

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