Potassium Carbonate → 1-Chloroisoquinolin-6-amine

HRID 1173121Notes

Reaction equation

HRID 1173121 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

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

Workup

  1. additionThe reaction solution was poured into 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-5b16ce11584f41a5b86faf34f50bfe80
Source dataset
uspto-grants-2010_11
Patent number
US07834049B2

Reaction notes

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