Azobisisobutyronitrile → 3-bromomethyl-7-chloro-1-(2-chloro-phenyl)-1H-quinolin-4-one

HRID 1887805Notes

Reaction equation

HRID 1887805 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:20])[C:7]([CH3:19])=[CH:8][N:9]2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])=[CH:4][CH:3]=1.[Br:21]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:21][CH2:19][C:7]1[C:6](=[O:20])[C:5]2[C:10](=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])[CH:8]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 712086007-chloro-1-(2-chloro-phenyl)-3-methyl-1H-quinolin-4-one

Product 1

HCID 866757663-bromomethyl-7-chloro-1-(2-chloro-phenyl)-1H-quinolin-4-one

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a 25 mL round-bottom flask was added 7-chloro-1-(2-chloro-phenyl)-3-methyl-1H-quinolin-4-one (324 mg, 1.07 mmol), N-bromosuccinimide (219 mg, 1.23 mmol), AIBN (33.0 mg, 201 μmol) and carbon tetrachloride (9 mL). The mixture was heated at reflux for 2 hr. The reaction mixture was cooled to room temperature and then placed in an ice bath. The solvent was decanted and the residue was then rinsed with a very small amount of dichloromethane. The supernatant was concentrated and the crude 3-bromomethyl-7-chloro-1-(2-chloro-phenyl)-1H-quinolin-4-one was used in the next step without further purification.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 hr
  3. customplaced in an ice bath
  4. customThe solvent was decanted
  5. washthe residue was then rinsed with a very small amount of dichloromethane
  6. concentrationThe supernatant was concentrated
  7. customthe crude 3-bromomethyl-7-chloro-1-(2-chloro-phenyl)-1H-quinolin-4-one was used in the next step without further purification

Sources & evidence

ORD record
ord-ab037395883348faa13d724ba1a628d8
Source dataset
uspto-grants-2013_08
Patent number
US08501732B2

Reaction notes

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