Azobisisobutyronitrile → HCID 90282020, compound

HRID 1497519Notes

Reaction equation

HRID 1497519 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[Br:19]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:19][CH2:1][C:2]1[CH:11]=[C:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 63896453HCID 63896453, compound

Product 1

HCID 90282020HCID 90282020, compoundYield 42.9%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
90 °C

Procedure

To a mixture of tert-butyl 2-methylquinoline-4-carboxylate (4.61 g) and carbon tetrachloride (50.0 mL) were added N-bromosuccinimide (3.71 g) and azobisisobutyronitrile (156 mg), followed by stirring at 90° C. for 5 hours. The reaction suspension was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain tert-butyl 2-(bromomethyl)quinoline-4-carboxylate (2.62 g).

Workup

  1. filtrationThe reaction suspension was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-c753a68e25de42a6ab3211148a8e3469
Source dataset
uspto-grants-2015_12
Patent number
US09199927B2

Reaction notes

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