Carbon Tetrachloride → 2-(Chloromethyl)quinoline

HRID 914477Notes

Reaction equation

HRID 914477 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.N(C(C)(C)C#N)=NC(C)(C)C#N.C(Cl)(Cl)(Cl)[Cl:25]>>[Cl:25][CH2:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

4

Reactant 3

HCID 5943Carbon TetrachlorideHCID 6547AzobisisobutyronitrileHCID 70602-Methylquinoline

Product 1

HCID 203942-(Chloromethyl)quinoline

Procedure

2-Methylquinoline (5.0 g) was dissolved in carbon tetrachloride (25 mL), imide N-bromosuccinate (6.2 g) and 2,2′-azobisisobutyronitrile (AIBN) (57 mg) were added thereto, and the mixture was refluxed for 4 hr. After ice-cooling, the reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=5:1) to give the title compound (3.7 g) as a pale-yellow solid.

Workup

  1. temperaturethe mixture was refluxed for 4 hr
  2. temperatureAfter ice-cooling
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-3f16b6e0b89943e1ac8a3e70b9e94f3e
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

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