Hydrochloric Acid → 8-chloroisoquinoline

HRID 1175748Notes

Reaction equation

HRID 1175748 reaction equation
N[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[N:9][CH:8]=[CH:7]2.N([O-])=O.[Na+].[ClH:16]>O>[Cl:16][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[N:9][CH:8]=[CH:7]2

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 13927912Isoquinolin-8-amineHCID 23668193Sodium Nitrite

Product 1

HCID 6409548-chloroisoquinoline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 8-aminoisoquinoline (J. Med. Chem., 2005, 48, 744-52) (1 mmol) in concentrated hydrochloric acid was added a solution of sodium nitrite (1.2 mmol) in water. The diazotization was carried out at 0° C. The cold diazonium salt solution was added to a solution of cuprous chloride in concentrated hydrochloric acid at 0° C. The cold solution was warmed to room temperature and stirred at room temperature for 3 hours. After 3 hours, the solution was heated at 60° C. for 30 min. Reaction mixture was basified and extracted with diethyl ether. Ether was washed with cold concentrated sulfuric acid, brine. Ether was dried over anhydrous sodium sulfate and evaporated under vacuum. Crude residue was column purified to afford a pale yellow liquid.

Workup

  1. customwas carried out at 0° C
  2. waitAfter 3 hours
  3. temperaturethe solution was heated at 60° C. for 30 min
  4. customReaction mixture
  5. extractionextracted with diethyl ether
  6. washEther was washed with cold concentrated sulfuric acid, brine
  7. dry with materialEther was dried over anhydrous sodium sulfate
  8. customevaporated under vacuum
  9. custompurified
  10. customto afford a pale yellow liquid

Sources & evidence

ORD record
ord-17c8085b024f4236bd1953212cab8b2d
Source dataset
uspto-grants-2010_11
Patent number
US07842703B2

Reaction notes

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