Sodium hydride → 6-Bromo-2-[(4-methoxyphenyl)methyl]-1(2H)-isoquinolinone

HRID 404726Notes

Reaction equation

HRID 404726 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][CH:6]=[CH:5]2.[H-].[Na+].[CH3:15][O:16][C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Cl)=[CH:19][CH:18]=1>CC(N(C)C)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH2:21][C:20]1[CH:23]=[CH:24][C:17]([O:16][CH3:15])=[CH:18][CH:19]=1)[CH:6]=[CH:5]2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 158851826-Bromoisoquinolin-1(2H)-one

Product 1

HCID 575517716-Bromo-2-[(4-methoxyphenyl)methyl]-1(2H)-isoquinolinone

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

28.18 g (125.8 mmol) 6-Bromo-2H-isoquinolin-1-one (6) were dissolved in 200 ml Dimethylacetamide and 7.55 g (188.7 mmol) sodium hydride (60%) were added at room temperature. After stirring for 30 minutes, 29.94 g (188.7 mmol) 4-Methoxy-benzylchloride were added and stirring was continued at room temperature until complete conversion was detected. The solvent was removed under reduced pressure, the residue taken up in saturated sodium hydrogen carbonate-solution and extracted three times with dichloromethane. The organic layers were dried over magnesium sulfate and evaporated. Final purification was achieved by silicagel chromatography. Rt=1.93 min (Method B). Detected mass: 344.1 (M+H+).

Workup

  1. stirringstirring
  2. customwas continued at room temperature until complete conversion
  3. customThe solvent was removed under reduced pressure
  4. extractionextracted three times with dichloromethane
  5. dry with materialThe organic layers were dried over magnesium sulfate
  6. customevaporated
  7. customFinal purification

Sources & evidence

ORD record
ord-7a4840789e254bd2bb4bd6095b28ce99
Source dataset
uspto-grants-2014_06
Patent number
US08748614B2

Reaction notes

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