Dimethylformamide → 6-Bromo-2-(2-hydroxy-2-methylpropyl)isoquinolin-1(2H)-one

HRID 601686Notes

Reaction equation

HRID 601686 reaction equation
[H-].[Na+].CN(C)C=[O:6].[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.Br[CH2:21][C:22]([CH3:24])=[CH2:23]>O>[Br:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15](=[O:19])[N:14]([CH2:21][C:22]([OH:6])([CH3:24])[CH3:23])[CH:13]=[CH:12]2

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 3577853-Bromo-2-methyl-1-propeneHCID 158851826-Bromoisoquinolin-1(2H)-one

Product 1

HCID 231581986-Bromo-2-(2-hydroxy-2-methylpropyl)isoquinolin-1(2H)-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under nitrogen atmosphere, 23 mg of 60% of sodium hydride was added at 0° C. to 2 ml solution of dimethylformamide with 62 mg of 6-bromo-2H-isoquinoline-1-one, and the mixture was stirred for 30 30 min. Then, 0.055 ml of 3-bromo-2-methyl-propene was added at 0° C., and the mixture was 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, and dried with anhydrous sodium sulfate. The solvents were distilled outunder reduced pressure, and the residues were separated and purified by thin-layer chromatography (hexane/ethyl acetate=3/1). The obtained compounds were dissolved in concentrated hydrochloric acid, stirred at 100° C. for 3 hours, and then cooled down to room temperature. After making it alkaline with 50% sodium hydride aqueous solution, the mixture was stirred at room temperature for 3 hours. Cold water was added to the reaction solution, and extracted with chloroform. Chloroform layer was washed with saturated saline solution, and dried with anhydrous sodium sulfate. The solvents were distilled outunder reduced pressure, and the residues were separated and purified by thin-layer chromatography (hexane/ethyl acetate=3/1) to obtain 20 mg of the above compound as a white solid.

Workup

  1. stirringthe mixture was stirred 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. distillationThe solvents were distilled outunder reduced pressure
  6. customthe residues were separated
  7. custompurified by thin-layer chromatography (hexane/ethyl acetate=3/1)
  8. dissolutionThe obtained compounds were dissolved in concentrated hydrochloric acid
  9. stirringstirred at 100° C. for 3 hours
  10. stirringthe mixture was stirred at room temperature for 3 hours
  11. additionCold water was added to the reaction solution
  12. extractionextracted with chloroform
  13. washChloroform layer was washed with saturated saline solution
  14. dry with materialdried with anhydrous sodium sulfate
  15. distillationThe solvents were distilled outunder reduced pressure
  16. customthe residues were separated
  17. custompurified by thin-layer chromatography (hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-40bdf9ebdec94a74b5328ea93bc6fbc1
Source dataset
uspto-grants-2011_03
Patent number
US07902369B2

Reaction notes

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