2,8-Dimethylquinoline → HCID 86707438, compound

HRID 338896Notes

Reaction equation

HRID 338896 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([CH3:12])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[Br:13]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:13][CH2:12][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[N:3]=[C:2]([CH3:1])[CH:11]=[CH:10]2

Participants

5

Reactant 2

HCID 151012,8-DimethylquinolineHCID 67184N-bromobutanimide

Product 1

HCID 86707438HCID 86707438, compoundYield 33.3%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 2,8-dimethylquinoline (3.00 g, 19.1 mmol) in carbon tetrachloride (50 mL) were added benzoyl peroxide (0.0139 g, 0.057 mmol) and N-bromosuccinimide (3.57 g, 20.0 mmol). The reaction mixture was heated at reflux for 18 hours. The solid was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was dissolved in DCM (100 mL), washed with saturated sodium bicarbonate and brine, dried (sodium sulfate), filtered and concentrated under reduced pressure to give 8-(bromomethyl)-2-methylquinoline (1.50 g, 33.3%) as a solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 18 hours
  3. customThe solid was removed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. dissolutionThe residue was dissolved in DCM (100 mL)
  6. washwashed with saturated sodium bicarbonate and brine
  7. dry with materialdried (sodium sulfate)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-193f0f2594d6415da3e3d527d8e0f60b
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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