2-Methylquinoline → 2-(Bromomethyl)quinoline

HRID 1729093Notes

Reaction equation

HRID 1729093 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.[Br:12]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:12][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

5

Reactant 3

HCID 70602-MethylquinolineHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimide

Product 1

HCID 124174182-(Bromomethyl)quinolineYield 12,608%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of chinaldine (14.3 g, 0.1 mmol) and N-bromosuccinimide (17.8g, 0.1 mmol)in CCl4 (150 mL) was added benzoylperoxide (2.6 g, 0.025 mol) and the mixture was heated under reflux for 4 hours. The reaction mixture was cooled to room temperature and evaporated in vacuum. The residue was treated with 5% HBr solution, the precipitate was filtered offand the filtrate was treated with celite and then basified with NaHCO3solution. The product was extracted with ether and crystallized from petrolether to yield 2-(bromomethyl)-quinoline (2.8 g, 12.6%) as light tancrystals.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. customevaporated in vacuum
  4. additionThe residue was treated with 5% HBr solution
  5. filtrationthe precipitate was filtered
  6. additionthe filtrate was treated with celite
  7. extractionThe product was extracted with ether
  8. customcrystallized from petrolether

Sources & evidence

ORD record
ord-3367fa47ab214b69bf4f46758cb696bb
Source dataset
uspto-grants-1994_07
Patent number
US05331006

Reaction notes

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