Water → 4-Bromo-3-methyl-2-nitroaniline

HRID 1468969Notes

Reaction equation

HRID 1468969 reaction equation
[CH3:1][C:2]1[C:3]([N+:9]([O-:11])=[O:10])=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[Br:12]N1C(=O)CCC1=O.O>C(O)(=O)C>[Br:12][C:8]1[CH:7]=[CH:6][C:4]([NH2:5])=[C:3]([N+:9]([O-:11])=[O:10])[C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 690383-Methyl-2-nitroaniline

Product 1

HCID 235150384-Bromo-3-methyl-2-nitroanilineYield 87%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3-methyl-2-nitroaniline (6.2 g, 41 mmol) was dissolved in 150 mL acetic acid, stirred and treated in portions with N-bromosuccinimide (7.3 g, 41 mmol). After 1 h the mixture was poured into 400 mL water with stirring. The precipitated product was collected by filtration, washed well with water, and then taken up in 200 mL ethyl acetate. This solution was washed with 50 mL water, 50 mL saturated NaHCO3, 50 mL saturated NaCl, dried (Na2SO4) and evaporated under vacuum to give the title compound as a bright orange solid (8.2 g, 87%): 1H NMR (400 MHz, CDCl3) δ 7.44-7.33 (d, J=8.8 Hz, 1H), 6.62-6.49 (d, J=8.8 Hz, 1H), 4.75 (s, 2H), 2.41 (s, 3H); EIMS m/z 230.

Workup

  1. stirringwith stirring
  2. filtrationThe precipitated product was collected by filtration
  3. washwashed well with water
  4. washThis solution was washed with 50 mL water, 50 mL saturated NaHCO3, 50 mL saturated NaCl
  5. dry with materialdried (Na2SO4)
  6. customevaporated under vacuum

Sources & evidence

ORD record
ord-f9c065d60b934ebdab9235d1c600b56d
Source dataset
uspto-grants-2015_04
Patent number
US09006250B2

Reaction notes

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