Potassium Carbonate → 1-Chloroisoquinolin-6-amine

HRID 1005679Notes

Reaction equation

HRID 1005679 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([NH:12]S(C3C=CC(C)=CC=3)(=O)=O)=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[OH-].[Na+].C(=O)([O-])[O-].[K+].[K+]>S(=O)(=O)(O)O>[NH2:12][C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[C:2]([Cl:1])=[N:3][CH:4]=[CH:5]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 22674092HCID 22674092, compound

Product 1

HCID 226741141-Chloroisoquinolin-6-amineYield 76.81%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

In sulfuric acid (30 ml) was dissolved 3.323 g of 1-chloro-6-(4-toluenesulfonylamino)isoquinoline (Preparation Example 22), followed by stirring at room temperature overnight. The reaction mixture was poured onto ice, and basified by adding an aqueous sodium hydroxide and then potassium carbonate, followed by extracting with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and the solvent was evaporated, to give the title compound (1.37 g, 76.81%) as yellowish brown crystals.

Workup

  1. additionThe reaction mixture was poured onto ice
  2. extractionby extracting with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-8927afb08bf3404085eb186010fdaf96
Source dataset
uspto-grants-2004_09
Patent number
US06787534B2

Reaction notes

Loading…