N-bromobutanimide → HCID 69670883, compound

HRID 1191663Notes

Reaction equation

HRID 1191663 reaction equation
[CH2:1]([C:3]1[N:8]=[C:7]([C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:5][CH:4]=1)[CH3:2].[Br:13]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:13][CH:1]([C:3]1[N:8]=[C:7]([C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:5][CH:4]=1)[CH3:2]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 45082565Methyl 6-ethylpyridine-2-carboxylate

Product 1

HCID 69670883HCID 69670883, compoundYield 80.9%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of methyl 6-ethylpyridine-2-carboxylate (587 mg) in carbon tetrachloride (28.4 mL) were added N-bromosuccinimide (696 mg) and benzoyl peroxide (75%, 11.5 mg). The mixture was heated under reflux for 4 hours. The reaction mixture was allowed to cool to ambient temperature. The insoluble material was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (702 mg).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 4 hours
  3. customThe insoluble material was removed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-e05de18ebf70472293cf494139b7e276
Source dataset
uspto-grants-2014_03
Patent number
US08680120B2

Reaction notes

Loading…