Isoquinoline → 2-Aminoisoquinolinium Iodide

HRID 336980Notes

Reaction equation

HRID 336980 reaction equation
[NH2:1]OS(O)(=O)=O.[CH:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][N:8]=1.C(=O)([O-])[O-].[K+].[K+].[IH:23]>O>[I-:23].[NH2:1][N+:8]1[CH:9]=[CH:10][C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 8405IsoquinolineHCID 11430Potassium CarbonateHCID 24841Hydrogen iodideHCID 76284hydroxylamine-O-sulfonic acid

Product 1

HCID 108586012-Aminoisoquinolinium Iodide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of hydroxylamine-O-sulfonic acid (2) (2 g, 1 equiv.), water (10 mL) and isoquinoline (1) (6.3 mL, 3 equiv.) was heated at 90° C. for 2-3 h. Potassium carbonate (2.44 g, 1 equiv.) was added, and the water was evaporated. Ethanol (20-30 mL) was added to the solid residue, and insoluble potassium sulfate was filtered out. Hydroiodic acid (57%-67%, 1.34 mL, 1 equiv.) was added to the filtrate, and the resulting solution was placed in a freezer. The precipitate was filtered out, washed with ethanol, and dried in vacuo. Isolated products were used as such in further reactions. Yield of the product was 1.78 g.

Workup

  1. customthe water was evaporated
  2. additionEthanol (20-30 mL) was added to the solid residue, and insoluble potassium sulfate
  3. filtrationwas filtered out
  4. filtrationThe precipitate was filtered out
  5. washwashed with ethanol
  6. customdried in vacuo

Sources & evidence

ORD record
ord-99d1ba09ac324ed69b0ec79c47ada600
Source dataset
uspto-grants-2014_11
Patent number
US08889713B1

Reaction notes

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