Tetrahydrofuran → HCID 25233016, compound

HRID 1014302Notes

Reaction equation

HRID 1014302 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[NH:8][CH2:7][CH2:6]2.[H-].[Na+].[CH2:16]1COCC1>[NH4+].[Cl-]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[N:8]([CH3:16])[CH2:7][CH2:6]2

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 106073926-methoxy-3,4-dihydroisoquinolin-1(2H)-one

Product 1

HCID 25233016HCID 25233016, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 25517Ammonium ChlorideSolvent

Procedure

To a solution of 6-(methyloxy)-3,4-dihydro-1(2H)-isoquinolinone (5 g, 28.2 mmol) in THF (300 mL) was added NaH (1.35 g, 34.1 mmol) and the mixture was stirred for 30 min, then Mel (4.82 g, 33.87 mmol) was added. Stirring was maintained for 3 hours and then the solution was diluted with sat. NH4Cl (aq) and extracted with dichloromethane. The combined organic layer was concentrated under reduced pressure to afford 6-methoxy-2-methyl-3,4-dihydroisoquinolin-1(2H)-one(6.3 g, 100%).

Workup

  1. additionMel (4.82 g, 33.87 mmol) was added
  2. stirringStirring
  3. temperaturewas maintained for 3 hours
  4. extractionextracted with dichloromethane
  5. concentrationThe combined organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-30da1fe89eba47a2b85f700ec174fdb2
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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