Hydrogen Bromide → 5-Bromoquinoline

HRID 1371515Notes

Reaction equation

HRID 1371515 reaction equation
N[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.N([O-])=O.[Na+].[OH-].[Na+].[BrH:18]>O>[Br:18][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 119115-AminoquinolineHCID 14798Sodium HydroxideHCID 23668193Sodium Nitrite

Product 1

HCID 8173215-BromoquinolineYield 22%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

5-Aminoquinoline (5 g, 34.7 mmol) is dissolved in HBr 48% (15 mL) and water (15 mL) and then cooled to 0° C. A solution of NaNO2 (2.5 g, 36.2 mmol) in water (15 mL) is added over about 10 minutes. The mixture is stirred for about 30 minutes at 0° C. and then at r.t. for about 1.5 hours. The mixture is transferred to an addition funnel and 75° C. solution of CuBr is added over 30 minutes. The mixture is stirred for about 30 minutes and then allowed to cool to r.t., which is then stirred for another 2 hours. The mixture is cooled to 0° C. and adjusted to pH of about 14 with 5N NaOH. The solution is filtered, and the solids are washed with DCM. The aqueous layer is extracted with DCM (2×200 mL), and the organic fractions are combined and concentrated. The residue is chromatographed on silica gel to give about 1.6 g of 5-bromoquinoline (22%).

Workup

  1. waitat r.t. for about 1.5 hours
  2. customThe mixture is transferred to an addition funnel and 75° C.
  3. stirringThe mixture is stirred for about 30 minutes
  4. temperatureto cool to r.t.
  5. stirringwhich is then stirred for another 2 hours
  6. temperatureThe mixture is cooled to 0° C.
  7. filtrationThe solution is filtered
  8. washthe solids are washed with DCM
  9. extractionThe aqueous layer is extracted with DCM (2×200 mL)
  10. concentrationconcentrated
  11. customThe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-6fbecd5ca51f411dbf55bf1a770b9ed5
Source dataset
uspto-grants-2007_01
Patent number
US07157463B2

Reaction notes

Loading…