2,3-Dimethylquinoline → HCID 19706749, compound

HRID 726624Notes

Reaction equation

HRID 726624 reaction equation
[CH3:1][C:2]1[C:11]([CH3:12])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[Br:13]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:13][CH2:12][C:11]1[C:2]([CH3:1])=[N:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

4

Reactant 2

HCID 155912,3-DimethylquinolineHCID 67184N-bromobutanimide

Product 1

HCID 19706749HCID 19706749, compoundYield 33.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 2,3-dimethylquinoline (0.50 g, 3.2 mmol) in carbon tetrachloride (40 ml) benzoyl peroxide (100 mg) and N-bromosuccinimide (1.14 g, 6.4 mmol) were added. The reaction mixture was refluxed for 4 hours, and then cooled to room temperature. The precipitate was removed by filtration and the filtrate was evaporated in vacuo. The residue was flash chromatographed on silica gel with ethyl acetate/petroleum ether as the eluent to give 0.25 g of 3-bromomethyl-2-methylquinoline.

Workup

  1. temperatureThe reaction mixture was refluxed for 4 hours
  2. customThe precipitate was removed by filtration
  3. customthe filtrate was evaporated in vacuo
  4. customchromatographed on silica gel with ethyl acetate/petroleum ether as the eluent

Sources & evidence

ORD record
ord-e4d886bbd546474c9636b4997a85366a
Source dataset
uspto-grants-1998_01
Patent number
US05710139

Reaction notes

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