Benzoyl Peroxide → 7-Chloro-2-(chloromethyl)quinoline

HRID 1198530Notes

Reaction equation

HRID 1198530 reaction equation
[Cl:1]N1C(=O)CCC1=O.[Cl:9][C:10]1[CH:19]=[C:18]2[C:13]([CH:14]=[CH:15][C:16]([CH3:20])=[N:17]2)=[CH:12][CH:11]=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Cl:9][C:10]1[CH:19]=[C:18]2[C:13]([CH:14]=[CH:15][C:16]([CH2:20][Cl:1])=[N:17]2)=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 31398Chlorosuccinimide2×HCID 1383957-Chloro-2-methylquinoline

Product 1

HCID 109548447-Chloro-2-(chloromethyl)quinoline

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

N-Chlorosuccinimide (3.0 g, 22.5 mmol) was added in portions over 1 hour to a stirred solution of 7-chloroquinaldine (3.3 g, 18.5 mmol) and dibenzoyl peroxide (0.1 g) in carbon tetrachloride (100 ml) under reflux. The mixture was heated under reflux for 24 hours adding further N-chlorosuccinimide (0.5 g and 1.0 g) after 3 hours and 20 hours. The mixture was cooled and filtered and the filtrate was extracted with 2M hydrochloric acid (5×40 ml). The extract was basified and re-extracted with dichloromethane and the extract was dried and evaporated to give the product contaminated with 7-chloroqinaldine.

Workup

  1. temperatureunder reflux
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 24 hours
  4. custom20 hours
  5. temperatureThe mixture was cooled
  6. filtrationfiltered
  7. extractionthe filtrate was extracted with 2M hydrochloric acid (5×40 ml)
  8. extractionre-extracted with dichloromethane
  9. customthe extract was dried
  10. customevaporated
  11. customto give the product

Sources & evidence

ORD record
ord-d019c1d62c4746b7a582878aa8230969
Source dataset
uspto-grants-1994_01
Patent number
US05281593

Reaction notes

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