Chlorosuccinimide → 1-(4-Chlorophenyl)-5-chloromethylisoquinoline

HRID 1156865Notes

Reaction equation

HRID 1156865 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.[Cl: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][Cl: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 31398ChlorosuccinimideHCID 128518261-(4-Chlorophenyl)-5-methylisoquinoline

Product 1

HCID 128518301-(4-Chlorophenyl)-5-chloromethylisoquinolineYield 79.9%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To 100 ml of carbon tetrachloride was added 14 g of 1-(4-chlorophenyl)-5-methylisoquinoline. While the solution was heated under reflux and light was irradiated on it, 7.5 g of N-chlorosuccinimide 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, and dried, followed by distilling off the solvent. Recrystallization of the residue from ether-hexane afforded 12.7 g of 1-(4-chlorophenyl)-5-chloromethylisoquinoline as light yellow prisms having a melting point of 101° to 102.5° 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. distillationby distilling off the solvent
  11. customRecrystallization of the residue from ether-hexane

Sources & evidence

ORD record
ord-752ffafb60624379a2ffafd69b8c1595
Source dataset
uspto-grants-1982_06
Patent number
US04337256

Reaction notes

Loading…