Methylamine → 5-bromo-N-methyl-2-nitroaniline

HRID 2202834Notes

Reaction equation

HRID 2202834 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4](F)[CH:3]=1.[CH3:12][NH2:13]>CCO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([CH:3]=1)[NH:13][CH3:12]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 27833624-Bromo-2-fluoro-1-nitrobenzene

Product 1

HCID 106095305-bromo-N-methyl-2-nitroaniline

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-bromo-2-fluoro-1-nitrobenzene (25 g) in EtOH (100 ml) was added methylamine (40% in MeOH, 34.8 ml) at room temperature. The mixture was stirred at room temperature for 1 h. After being stirred, the reaction mixture was cooled to 0° C., and the precipitate was collected by filtration and washed with EtOH (0° C.) and IPE. The solid was dried to give the title compound (24.8 g) as a yellow solid.

Workup

  1. stirringAfter being stirred
  2. temperaturethe reaction mixture was cooled to 0° C.
  3. filtrationthe precipitate was collected by filtration
  4. washwashed with EtOH (0° C.) and IPE
  5. customThe solid was dried

Sources & evidence

ORD record
ord-c971dfd365bd470bb5e1c61a72445fdb
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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