Hydrogen Bromide → 5-Bromoisoquinoline

HRID 910077Notes

Reaction equation

HRID 910077 reaction equation
N([O-])=O.[Na+].N[C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[CH:8]=[CH:9][N:10]=[CH:11]2.[OH-].[Na+].[BrH:18]>O>[Br:18][C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[CH:8]=[CH:9][N:10]=[CH:11]2

Participants

6

Reactant 4

HCID 260Hydrogen Bromide2×HCID 14798Sodium HydroxideHCID 707665-AminoisoquinolineHCID 23668193Sodium Nitrite

Product 1

HCID 7364875-Bromoisoquinoline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

Add a solution of sodium nitrite (9.6 g, 139 mmol) in water (50 mL) cautiously to 5-aminoisoquinoline (20 g, 139 mmol) in hydrobromic acid (48%, 100 mL) at 0° C. Transfer this mixture to a vessel containing CuBr (25 g, 174 mmol) in hydrobromic acid (48%, 200 mL) at 75° C. After complete addition, stir the mixture at 75° C. for one hour, cool to room temperature and stir overnight. Place the mixture in an ice bath, add ice to the reaction mixture, and then add sodium hydroxide aqueous solution (20%, 250 mL). Filter the slurry and extract the filtrate with diethyl ether. Combine the solid and the extract sonicate for one hour in chloroform. Filter the suspension through a plug of Celite™, and concentrate the filtrate under reduced pressure. Subject the residue to silica gel chromatography, eluting with chloroform.

Workup

  1. additionAfter complete addition
  2. temperaturecool to room temperature
  3. stirringstir overnight
  4. additionadd ice to the reaction mixture
  5. filtrationFilter the slurry
  6. extractionextract the filtrate with diethyl ether
  7. customthe extract sonicate for one hour in chloroform
  8. filtrationFilter the suspension through a plug of Celite™
  9. concentrationconcentrate the filtrate under reduced pressure
  10. washeluting with chloroform

Sources & evidence

ORD record
ord-471e9e03c0fe4099bd38427e0eeb48e7
Source dataset
uspto-grants-2011_09
Patent number
US08022065B2

Reaction notes

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