N-bromobutanimide → HCID 19706754, compound

HRID 726628Notes

Reaction equation

HRID 726628 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[C:6]([CH3:13])=[CH:5]2.[Br:14]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:14][CH2:13][C:6]1[C:7]([CH3:12])=[N:8][C:9]2[C:4]([CH:5]=1)=[CH:3][C:2]([Cl:1])=[CH:11][CH:10]=2

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 19706717HCID 19706717, compound

Product 1

HCID 19706754HCID 19706754, compoundYield 31.7%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 6-chloro-2,3-dimethylquinoline (2.0 g, 10.5 mmol) in carbon tetrachloride (80 ml) benzoyl peroxide (100 mg) and N-bromosuccinimide (3.7 g, 21.0 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 0.90 g 3-bromomethyl-6-chloro-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-e0ea45de1af44a338528174bff00ce6b
Source dataset
uspto-grants-1998_01
Patent number
US05710139

Reaction notes

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