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

HRID 420468

Reaction equation

HRID 420468 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-f90601c1bdb344d6b84112a3453fbf50
Source dataset
uspto-grants-2012_01
Patent number
US08097349B2

Linked notes

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