Acetic Acid → 4-Bromo-N-methyl-2-nitroaniline

HRID 2262439Notes

Reaction equation

HRID 2262439 reaction equation
C(O)(=O)C.[CH3:5][NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-:15])=[O:14].[Br:16]N1C(=O)CCC1=O>O>[Br:16][C:10]1[CH:11]=[CH:12][C:7]([NH:6][CH3:5])=[C:8]([N+:13]([O-:15])=[O:14])[CH:9]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 67184N-bromobutanimideHCID 69157Benzenamine, N-methyl-2-nitro-

Product 1

HCID 2580424-Bromo-N-methyl-2-nitroanilineYield 93.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Pouring 60 milliliter of acetic acid over 5.0 g (33 mmol) of N-methyl-2-nitroaniline and 5.9 g (33 mmol) of N-bromosuccinimide, the resultant solution was refluxed with heating for 7 hours. After completion of the reaction, the reacted solution was poured into 500 milliliter of water, and precipitated solids were separated with filtration. Dissolving the resultant solids into ethyl acetate, the resultant solution was dried with the use of magnesium sulfate. After filtration, the solvent was removed by distillation under reduced pressure, and after drying the solids under reduced pressure at room temperature, 7.1 g of 4-bromo-N-methyl-2-nitroaniline as orange solids were obtained (yield: 93%).

Workup

  1. temperaturewith heating for 7 hours
  2. customAfter completion of the reaction
  3. customprecipitated solids
  4. customwere separated with filtration
  5. dissolutionDissolving the resultant solids into ethyl acetate
  6. dry with materialthe resultant solution was dried with the use of magnesium sulfate
  7. filtrationAfter filtration
  8. customthe solvent was removed by distillation under reduced pressure
  9. customafter drying the solids under reduced pressure at room temperature

Sources & evidence

ORD record
ord-e4b1401a680f4e77a45beba3d08217cf
Source dataset
uspto-grants-2010_12
Patent number
US07851071B2

Reaction notes

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