Methylamine → 4-Bromo-N-methyl-2-nitroaniline

HRID 1403522Notes

Reaction equation

HRID 1403522 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](F)=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:18][NH2:19]>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:19][CH3:18])=[C:4]([N+:9]([O-:11])=[O:10])[CH:3]=1

Participants

5

Reactant 3

HCID 6329MethylamineHCID 11430Potassium CarbonateHCID 27363284-Bromo-1-fluoro-2-nitrobenzene

Product 1

HCID 2580424-Bromo-N-methyl-2-nitroanilineYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-bromo-1-fluoro-2-nitrobenzene (6 g, 27.27 mmol) in dichloromethane (100 ml) was added potassium carbonate (7.5 g, 54.27 mmol). This was followed by the addition of CH3NH2 (20 ml, 33% aqueous), which was added dropwise with stirring at room temperature. The resulting solution was stirred for 2 h at room temperature, extracted with dichloromethane (2×200 ml), and the organic layers combined and concentrated under vacuum to afford 4-bromo-N-methyl-2-nitroaniline as a red solid (6.1 g, 97%).

Workup

  1. additionwas added dropwise
  2. stirringThe resulting solution was stirred for 2 h at room temperature
  3. extractionextracted with dichloromethane (2×200 ml)
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-43116106268e4ea0999c6d9ea153ebec
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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