Dimethylformamide → 6-Bromo-2-methyl-1,2-dihydroisoquinolin-1-one

HRID 601665Notes

Reaction equation

HRID 601665 reaction equation
[Na].[CH3:2][N:3]([CH3:6])[CH:4]=[O:5].[Br:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)C(=O)NC=[CH:11]2.CI>O>[Br:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[C:4](=[O:5])[N:3]([CH3:6])[CH:2]=[CH:11]2

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 5360545SodiumHCID 158851826-Bromoisoquinolin-1(2H)-one

Product 1

HCID 231581786-Bromo-2-methyl-1,2-dihydroisoquinolin-1-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under nitrogen atmosphere, 60% sodium hydrogenate (18 mg) was added at 0° C. to 2 ml solution of dimethylformamide with 100 mg of 6-bromo-2H-isoquinoline-1-one, and the mixture was stirred for 30 min. Then, 0.03 ml of methyl iodide was added at 0° C., stirred at room temperature for 2 hours. Cold water was added to the reaction solution, extracted with chloroform. Chloroform layer was washed with saturated saline solution, dried with anhydrous sodium sulfate. After distilling out the solvents under reduced pressure, residues were separated and purified by preparative thin-layer chromatography (hexane/ethyl acetate=3/1) to obtain 24 mg of the above compound as a white solid.

Workup

  1. stirringstirred at room temperature for 2 hours
  2. extractionextracted with chloroform
  3. washChloroform layer was washed with saturated saline solution
  4. dry with materialdried with anhydrous sodium sulfate
  5. distillationAfter distilling out the solvents under reduced pressure, residues
  6. customwere separated
  7. custompurified by preparative thin-layer chromatography (hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-b86dfcfee9a4441da597a101163ffdfa
Source dataset
uspto-grants-2011_03
Patent number
US07902369B2

Reaction notes

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