Azobisisobutyronitrile → HCID 66737125, compound

HRID 599359Notes

Reaction equation

HRID 599359 reaction equation
[Br:1]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N.[CH3:21][O:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[N:29]=[CH:28][CH:27]=[C:26]2[CH3:33]>C1C=CC=CC=1>[Br:1][CH2:33][C:26]1[C:25]2[C:30](=[CH:31][CH:32]=[C:23]([O:22][CH3:21])[CH:24]=2)[N:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 6547Azobisisobutyronitrile2×HCID 67184N-bromobutanimideHCID 2587616-Methoxy-4-methylquinoline

Product 1

HCID 66737125HCID 66737125, compoundYield 19.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

N-Bromosuccinimide (0.92 g, 5.2 mmol) and 2,2′-azobisisobutyronitrile (0.095 g, 0.58 mmol) were added to a solution of 6-methoxy-4-methylquinoline (1.0 g, 5.8 mmol) in anhydrous benzene (15 mL) at room temperature, and the mixture was stirred for 5 hours under reflux. Further 2,2′-azobisisobutyronitrile (0.19 g, 1.2 mmol) was added thereto, and the mixture was stirred for 17 hours under reflux. The solvent was evaporated under reduced pressure, and the resulting residue was roughly purified by silica gel chromatography to give 0.26 g of mixture containing the title Reference Compound as green oil.

Workup

  1. temperatureunder reflux
  2. stirringthe mixture was stirred for 17 hours
  3. temperatureunder reflux
  4. customThe solvent was evaporated under reduced pressure
  5. customthe resulting residue was roughly purified by silica gel chromatography

Sources & evidence

ORD record
ord-2e3ec379ba194a2b88e067aa7b66d5c7
Source dataset
uspto-grants-2011_03
Patent number
US07897774B2

Reaction notes

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