N-bromobutanimide → 1-(4-Chlorophenyl)-5-bromomethylisoquinoline

HRID 1156864Notes

Reaction equation

HRID 1156864 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[C:13]([CH3:18])[CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[Br:19]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[C:13]([CH2:18][Br:19])[CH:14]=[CH:15][CH:16]=3)[CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 128518261-(4-Chlorophenyl)-5-methylisoquinoline

Product 1

HCID 128518271-(4-Chlorophenyl)-5-bromomethylisoquinolineYield 68.8%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

1-(4-Chlorophenyl)-5-methylisoquinoline (10.2 g) was dissolved in 50 ml of carbon tetrachloride. While the solution was heated under reflux and light was irradiated on it, 7.5 g of N-bromosuccinimide was added. The mixture was heated with stirring. After the reaction, the reaction mixture was cooled. The insoluble matter was removed by filtration. The filtrate was washed in water, dried, and concentrated to remove the solvent. Recrystallization from cold methanol afforded 9.2 g of 1-(4-chlorophenyl)-5-bromomethylisoquinoline as colorless needles having a decomposition point of 116° C.

Workup

  1. temperatureWhile the solution was heated
  2. temperatureunder reflux
  3. additionwas added
  4. temperatureThe mixture was heated
  5. customAfter the reaction
  6. temperaturethe reaction mixture was cooled
  7. customThe insoluble matter was removed by filtration
  8. washThe filtrate was washed in water
  9. customdried
  10. concentrationconcentrated
  11. customto remove the solvent
  12. customRecrystallization from cold methanol

Sources & evidence

ORD record
ord-49a308e0284b4c63ae486e6459490b57
Source dataset
uspto-grants-1982_06
Patent number
US04337256

Reaction notes

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