5-Hydroxy-1(2H)-isoquinolinone → HCID 21390339, compound

HRID 462051Notes

Reaction equation

HRID 462051 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:3]=1[CH:4]=[CH:5][NH:6][C:7]2=[O:8].[CH2:13]1[O:15][CH:14]1[CH2:16][OH:17]>[OH-].[Na+]>[OH:15][CH:14]([CH2:16][OH:17])[CH2:13][O:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:3]=1[CH:4]=[CH:5][NH:6][C:7]2=[O:8]

Participants

4

Reactant 2

HCID 13405-Hydroxy-1(2H)-isoquinolinoneHCID 11164Glycidol

Product 1

HCID 21390339HCID 21390339, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

16 g of 5-hydroxyisocarbostyril was dissolved in 110 ml of a 1N aqueous sodium hydroxide solution, and 8 g of glycidol was added to the solution. The mixture was then refluxed for 2 hours while stirring. After allowing the mixture to cool, the precipitated crystals were filtered, and recrystallized from water to give 20 g of 5-(2,3-dihydroxy)propoxyisocarbostyril as colorless needle-like crystals having a melting point of 228° - 230° C.

Workup

  1. additionwas added to the solution
  2. temperatureThe mixture was then refluxed for 2 hours
  3. temperatureto cool
  4. filtrationthe precipitated crystals were filtered
  5. customrecrystallized from water

Sources & evidence

ORD record
ord-54e2f499958f42afa163f629e4efd18b
Source dataset
uspto-grants-1977_12
Patent number
US04065456

Reaction notes

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