HCID 21393810, compound → HCID 21393805, compound

HRID 1288482Notes

Reaction equation

HRID 1288482 reaction equation
[Cl:1][C:2]1[C:3]([O:13]C)=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[N:9][CH:8]=[C:7]2[CH3:12]>Br>[ClH:1].[Cl:1][C:2]1[C:3]([OH:13])=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[N:9][CH:8]=[C:7]2[CH3:12]

Participants

3

Reactant 1

HCID 21393810HCID 21393810, compound

Product 1

HCID 21393805HCID 21393805, compound

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

8-Chloro-7-methoxy-4-methylisoquinoline (0.89 g.) in 48% hydrobromic acid is refluxed for 48 hours. The mixture is evaporated to dryness in vacuo, redissolved in water and neutralized with ammonium hydroxide. The mixture is cooled and the precipitate is filtered off and treated with hydrogen chloride in ethanol. Ether is added and the precipitate is filtered off to give 8-chloro-7-hydroxy-4-methylisoquinoline hydrochloride.

Workup

  1. customThe mixture is evaporated to dryness in vacuo
  2. dissolutionredissolved in water and neutralized with ammonium hydroxide
  3. temperatureThe mixture is cooled
  4. filtrationthe precipitate is filtered off
  5. additiontreated with hydrogen chloride in ethanol
  6. additionEther is added
  7. filtrationthe precipitate is filtered off

Sources & evidence

ORD record
ord-397bae504de14eeab42c3654c9253be4
Source dataset
uspto-grants-1976_10
Patent number
US03988339

Reaction notes

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