Azobisisobutyronitrile → 3-Methoxy-2-nitro-6-pyridylmethyl bromide

HRID 1193963

Reaction equation

HRID 1193963 reaction equation
N(C(C)(C)C#N)=NC(C)(C)C#N.[CH3:13][O:14][C:15]1[C:16]([N+:22]([O-:24])=[O:23])=[N:17][C:18]([CH3:21])=[CH:19][CH:20]=1.[Br:25]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[CH3:13][O:14][C:15]1[C:16]([N+:22]([O-:24])=[O:23])=[N:17][C:18]([CH2:21][Br:25])=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 27279653-Methoxy-6-methyl-2-nitropyridine

Product 1

HCID 144051243-Methoxy-2-nitro-6-pyridylmethyl bromideYield 21.3%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A catalytic amount of α,α'-azobis(isobutyronitrile) was added to 3-methoxy-6-methyl-2-nitropyridine (described in Acta Chem. Scand., vol. 23, pages 1791-1796) (7.1 g), N-bromosuccinimide (7.1 g) and carbon tetrachloride (80 ml), and the mixture was refluxed for 16 hours. After the reaction, while the reaction mixture was still hot, it was suction-filtered to separate the insoluble succinimide. The filtrate was cooled to room temperature whereupon the unreacted 3-methoxy-6-methyl-2-nitropyridine precipitated as crystals. The crystals were separated by filtration. The residue was concentrated and then vacuum distilled to give 3-methoxy-2-nitro-6-pyridylmethyl bromide (2.1 g).

Workup

  1. temperaturethe mixture was refluxed for 16 hours
  2. customAfter the reaction
  3. filtrationit was suction-filtered
  4. customto separate the insoluble succinimide
  5. customprecipitated as crystals
  6. customThe crystals were separated by filtration
  7. concentrationThe residue was concentrated
  8. distillationvacuum distilled

Sources & evidence

ORD record
ord-622dd790ec964bd2ae5b882309c91154
Source dataset
uspto-grants-1989_03
Patent number
US04812454

Linked notes

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