N-bromobutanimide → HCID 20772210, compound

HRID 1814765Notes

Reaction equation

HRID 1814765 reaction equation
[CH3:1][O:2][C:3]1[C:4]([N+:10]([O-:12])=[O:11])=[N:5][C:6]([CH3:9])=[CH:7][CH:8]=1.BrN1C(=[O:19])CCC1=O>C(Cl)(Cl)(Cl)Cl.[W]>[CH3:1][O:2][C:3]1[C:4]([N+:10]([O-:12])=[O:11])=[N:5][C:6]([CH:9]=[O:19])=[CH:7][CH:8]=1

Participants

5

Reactant 2

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

Product 1

HCID 20772210HCID 20772210, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 23964TungstenCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 3-methoxy-6-methyl-2-nitropyridine (S. Lindstrom, T. Ahmad and S. Grivas, Heterocycles (1994), 38(3), 529-540) (30 mmole) and N-bromosuccinimide (60 mmole) in CCl4 (50 ml) was refluxed under a 500 watt tungsten lamp for 16 hours, cooled, filtered and evaporated. A portion (2.4 g) of the crude product was mixed with sodium formate (1 g), water (1 ml) and ethanol (7 ml), refluxed for 24 hours, cooled and concentrated to low volume. The residue was partitioned between dichloromethane and water, the organic dried and evaporated. Chromatography gave the title compound (25%).

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. customevaporated
  4. additionA portion (2.4 g) of the crude product was mixed with sodium formate (1 g), water (1 ml) and ethanol (7 ml)
  5. temperaturerefluxed for 24 hours
  6. temperaturecooled
  7. concentrationconcentrated to low volume
  8. customThe residue was partitioned between dichloromethane and water
  9. customthe organic dried
  10. customevaporated

Sources & evidence

ORD record
ord-dccc482b9f9e4a1ab7e2b8aab64b9afe
Source dataset
uspto-grants-2005_04
Patent number
US06878704B2

Reaction notes

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