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

HRID 2405464Notes

Reaction equation

HRID 2405464 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

60 mL of acetic acid was added to 5.0 g (33 mmol) of N-methyl-2-nitroaniline and 5.9 g (33 mmol) of N-bromosuccinimide. The mixture was heat refluxed for 7 hours. After completion of the reaction, the reaction solution was poured into 500 mL of water, and a solid that precipitated by this operation was collected by filtration. The solid was dissolved in ethyl acetate, and dried over magnesium sulfate. After filtering the solution, the solvent was evaporated under reduced pressure. The residue was dried at room temperature under reduced pressure to obtain 7.1 g of 4-bromo-N-methyl-2-nitroaniline as an orange solid (yield: 93%).

Workup

  1. temperatureThe mixture was heat
  2. temperaturerefluxed for 7 hours
  3. customAfter completion of the reaction
  4. customa solid that precipitated by this operation
  5. filtrationwas collected by filtration
  6. dissolutionThe solid was dissolved in ethyl acetate
  7. dry with materialdried over magnesium sulfate
  8. filtrationAfter filtering the solution
  9. customthe solvent was evaporated under reduced pressure
  10. customThe residue was dried at room temperature under reduced pressure

Sources & evidence

ORD record
ord-290b53b96d314c3695c7d9bfba99e45e
Source dataset
uspto-grants-2014_08
Patent number
US08803420B2

Reaction notes

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