Azobisisobutyronitrile → HCID 22320276, compound

HRID 498048Notes

Reaction equation

HRID 498048 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]2[N:12]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)[N:13]=[C:14]([CH3:15])[C:3]=12.[Br:22]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:22][CH2:15][C:14]1[C:3]2[C:4](=[N:5][C:6]3[C:11]([C:2]=2[Cl:1])=[CH:10][CH:9]=[CH:8][CH:7]=3)[N:12]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)[N:13]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 223201094-Chloro-3-methyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]quinoline

Product 1

HCID 22320276HCID 22320276, compoundYield 53.5%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of 4-chloro-3-methyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]quinoline (1.22 g, 4.1 mmol), N-bromosuccinimide (0.87 g, 4.9 mmol) and 2,2′-azobis(isobutyronitrile) (66 mg, 0.4 mmol) in carbon tetrachloride (40 mL) was heated under reflux under an argon atmosphere for 3 hours. The solution was allowed to cool to room temperature, the insoluble solid was removed and the solution was concentrated under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (hexane:chloroform:ethyl acetate=2:1:1) to give the title compound (0.82 g, 53% yield).

Workup

  1. temperatureunder reflux under an argon atmosphere for 3 hours
  2. customthe insoluble solid was removed
  3. concentrationthe solution was concentrated under reduced pressure
  4. customThe residue thus obtained
  5. customwas purified by silica gel column chromatography (hexane:chloroform:ethyl acetate=2:1:1)

Sources & evidence

ORD record
ord-46ad609b604d4f8191dd0a8d9f7d0586
Source dataset
uspto-grants-2005_09
Patent number
US06949648B2

Reaction notes

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