Dimethylformamide → 6-bromo-2-ethylisoquinolin-1(2H)-one

HRID 601671Notes

Reaction equation

HRID 601671 reaction equation
[H-].[Na+].CN(C)C=O.[Br:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15](=[O:19])[NH:14][CH:13]=[CH:12]2.[CH2:20](I)[CH3:21]>O>[Br:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15](=[O:19])[N:14]([CH2:20][CH3:21])[CH:13]=[CH:12]2

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 158851826-Bromoisoquinolin-1(2H)-one

Product 1

HCID 231582376-bromo-2-ethylisoquinolin-1(2H)-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under nitrogen atmosphere, 22 mg of 60% sodium hydride was added at 0° C. to 3 ml solution of dimethylformamide with 100 mg of 6-bromo-2H-isoquinoline-1-one, and the mixture was stirred for 30 min. 0.04 ml of ethyl iodide was added at 0° C., and the mixture was stirred at room temperature for 3 hours. Cold water was added to the reaction solution, extracted with chloroform. Chloroform layer was washed with saturated saline solution, and dried with anhydrous sodium sulfate. After distilling out the solvents under reduced pressure, the residues were separated and purified by thin-layer chromatography (hexane/ethyl acetate=3/1) to obtain 30 mg of the above compound as a white solid.

Workup

  1. stirringthe mixture was stirred at room temperature for 3 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
  6. customthe residues were separated
  7. custompurified by thin-layer chromatography (hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-b8eb0ecac35e4cbd9356f58d2effc9a0
Source dataset
uspto-grants-2011_03
Patent number
US07902369B2

Reaction notes

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