Sodium methanethiolate → 6-Isoquinolinol, 7-bromo-

HRID 228878Notes

Reaction equation

HRID 228878 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[CH:9]2)=[CH:4][C:3]=1[O:12]C.C[S-].[Na+]>CN(C)C=O>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[CH:9]2)=[CH:4][C:3]=1[OH:12]

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 230784917-Bromo-6-methoxyisoquinoline

Product 1

HCID 1358548376-Isoquinolinol, 7-bromo-Yield 23.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

7-Bromo-6-methoxyisoquinoline (50 mg) and sodium thiomethoxide (147 mg) were suspended in N,N-dimethylformamide (2 ml), and the suspensioin was stirred at 150° C. for 2 hr. The reaction solution was cooled to room temperature, the reaction solution was then filtered, and the solvent was removed from the filtrate by distillation under the reduced pressure. The residue was purified by thin layer chromatography using chloroform-methanol to give 7-bromo-6-hydroxyisoquinoline (11 mg, yield 22%).

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. filtrationthe reaction solution was then filtered
  3. customthe solvent was removed from the filtrate by distillation under the reduced pressure
  4. customThe residue was purified by thin layer chromatography

Sources & evidence

ORD record
ord-79cd1e5009574c81aaab3218a78ba9d0
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Reaction notes

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