5-Hydroxy-1(2H)-isoquinolinone → HCID 10037793, compound

HRID 1887234Notes

Reaction equation

HRID 1887234 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][NH:6][C:7]2=[O:12].[OH-].[K+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CO>[CH2:15]([O:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][NH:6][C:7]2=[O:12])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 13405-Hydroxy-1(2H)-isoquinolinoneHCID 7498Benzyl BromideHCID 14797Potassium Hydroxide

Product 1

HCID 10037793HCID 10037793, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Hydroxyisoquinolin-1(2H)-one (0.65 g, 4.04 mmol) was added in portions to a solution of potassium hydroxide (0.23 g, 4.04 mmol) in methanol (15 mL). The mixture was stirred at ambient temperature for 10 minutes, then benzyl bromide (0.69 g, 0.48 mL, 4.04 mmol) was added. The mixture was stirred at ambient temperature for 30 minutes and then at 40° C. for 2 hours. The solvent was removed in vacuo. The residue was dissolved in dichloromethane (100 mL) and washed with water (100 mL). The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo. The residue was recrystallized from methanol (10 mL) to afford the title compound (0.40 g, 40%): mp 165-168° C.; MS (ES+) m/z 252.1 (M+1).

Workup

  1. stirringThe mixture was stirred at ambient temperature for 30 minutes
  2. waitat 40° C. for 2 hours
  3. customThe solvent was removed in vacuo
  4. dissolutionThe residue was dissolved in dichloromethane (100 mL)
  5. washwashed with water (100 mL)
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated in vacuo
  9. customThe residue was recrystallized from methanol (10 mL)

Sources & evidence

ORD record
ord-ebc9bd955a17469e8002aa110097cf3d
Source dataset
uspto-grants-2013_08
Patent number
US08501746B2

Reaction notes

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