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

HRID 1172767Notes

Reaction equation

HRID 1172767 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N+:9]([O-:11])=[O:10].[Br:12]N1C(=O)CCC1=O.C(O)(=O)C>O>[Br:12][C:6]1[CH:7]=[CH:8][C:3]([NH:2][CH3:1])=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=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%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5.0 g (33 mmol) of N-methyl-2-nitroaniline and 5.9 g (33 mmol) of N-bromosuccinimide were added with 60 mL of acetic acid, and the whole was refluxed under heating for 7 hours. After the completion of the reaction, the reaction solution was poured into 500 mL of water, and the precipitated solid was filtered out. The solid that had been filtered out was dissolved into ethyl acetate and dried with magnesium sulfate. After filtration, the solvent was distilled off under reduced pressure, and the residue was dried at room temperature under reduced pressure to obtain 7.1 g of the orange solid of 4-bromo-N-methyl-2-nitroaniline (93% yield).

Workup

  1. temperaturethe whole was refluxed
  2. temperatureunder heating for 7 hours
  3. customAfter the completion of the reaction
  4. filtrationthe precipitated solid was filtered out
  5. filtrationThe solid that had been filtered out
  6. dissolutionwas dissolved into ethyl acetate
  7. dry with materialdried with magnesium sulfate
  8. filtrationAfter filtration
  9. distillationthe solvent was distilled off under reduced pressure
  10. customthe residue was dried at room temperature under reduced pressure

Sources & evidence

ORD record
ord-ae3b6be193a64172b56e911a0eb0dfe3
Source dataset
uspto-grants-2010_11
Patent number
US07833632B2

Reaction notes

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