1-Methylisoquinoline → 1-Bromomethylisoquinoline

HRID 446895Notes

Reaction equation

HRID 446895 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.C1C(=O)N([Br:19])C(=O)C1>CC(N=NC(C#N)(C)C)(C#N)C.C(Cl)(Cl)(Cl)Cl>[Br:19][CH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 155921-MethylisoquinolineHCID 67184N-bromobutanimide

Product 1

HCID 27762461-BromomethylisoquinolineYield 18%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To 1-methylisoquinoline (0.99 g, 6.91 mmol), NBS (1.35 g, 1.1 eq) and AIBN (10 mg, catalytic amount) was added CCl4 (15 mL), which was then refluxed for 2 h. The suspended particles were removed by filtration, and washed with CCl4. The organic layers were combined, concentrated under reduced pressure, and separated by column chromatography (30%, ethyl acetate/hexane) to give the title compound (270 mg, Yield: 18%) as a violet solid.

Workup

  1. temperaturewas then refluxed for 2 h
  2. customThe suspended particles were removed by filtration
  3. washwashed with CCl4
  4. concentrationconcentrated under reduced pressure
  5. customseparated by column chromatography (30%, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-000f1e70c96942e2955d1c1ed2f56261
Source dataset
uspto-grants-2013_07
Patent number
US08481537B2

Reaction notes

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