Azobisisobutyronitrile → HCID 86643710, compound

HRID 1672860Notes

Reaction equation

HRID 1672860 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([C:9]#[N:10])[N:3]=1.[Br:11]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:11][CH2:8][C:7]1[C:2]([Cl:1])=[N:3][C:4]([C:9]#[N:10])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 573644776-Chloro-5-methylpyridine-2-carbonitrile

Product 1

HCID 86643710HCID 86643710, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

2-Chloro-6-cyano-3-methylpyridine (92.0 mg, 0.603 mmol) obtained in Step 2 was dissolved in carbon tetrachloride (4 mL), and the mixture was stirred for 1 hour under reflux after adding N-bromosuccinimide (118 mg, 0.663 mmol) and α,α-azobisisobutyronitrile (9.90 mg, 0.0603 mmol). The mixture was concentrated under reduced pressure, and the resulting residue was purified by preparative TLC to give 3-bromomethyl-2-chloro-6-cyanopyridine (55.8 mg, 40%).

Workup

  1. temperatureunder reflux
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customthe resulting residue was purified by preparative TLC

Sources & evidence

ORD record
ord-7d34bfc8be8a4ad488a927da221f98d7
Source dataset
uspto-grants-2011_08
Patent number
US07998954B2

Reaction notes

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