Hydrogen Bromide → HCID 23155929, compound

HRID 1714809Notes

Reaction equation

HRID 1714809 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][N:9]=[C:10]2[N:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]2)=[CH:5][CH:4]=1.Br.[OH-].[Na+]>>[OH:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][N:9]=[C:10]2[N:13]2[CH2:14][CH2:15][N:16]([CH3:19])[CH2:17][CH2:18]2)=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 23155659HCID 23155659, compound

Product 1

HCID 23155929HCID 23155929, compoundYield 89.5%

Procedure

A mixture of 795 mg of 7-methoxy-(4-methylpiperazin-1-yl)-isoquinoline and 8 ml of 47% aqueous hydrobromic acid solution was heated under reflux for 2.5 hours. After cooling, the solution was neutralized with 20% aqueous sodium hydroxide solution, extracted with chloroform, dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was purified on silica gel column chromatography (saturated ammonia water:methanol:chloroform=1:10:90) to provide 673 mg (80%) of 7-hydroxy-1-(4-methylpiperazin-1-yl)isoquinoline.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2.5 hours
  3. temperatureAfter cooling
  4. extractionextracted with chloroform
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified on silica gel column chromatography (saturated ammonia water:methanol:chloroform=1:10:90)

Sources & evidence

ORD record
ord-1f478d08c6b4427aa3ea0de816870895
Source dataset
uspto-grants-2010_09
Patent number
US07799775B2

Reaction notes

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