Methylamine → N-Methyl-4-nitroaniline

HRID 1910765Notes

Reaction equation

HRID 1910765 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH3:11][NH2:12]>>[CH3:11][NH:12][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 6329MethylamineHCID 74741-Chloro-4-nitrobenzene

Product 1

HCID 7483N-Methyl-4-nitroanilineYield 93%

Procedure

1-Chloro-4-nitro-benzene (5.0 g, 31.7 mmol) was added to excess aqueous methylamine solution-(40%, 30 mL) and heated in a pressure bomb for 16 h. The reaction mass was cooled to room temperature and a solid filtered off. The filtrate was evaporated to dryness and the combined solids were purified by trituration with pentane to afford methyl-(4-nitro-phenyl)-amine (4.5 g, 93%) as a solid.

Workup

  1. temperatureheated in a pressure bomb for 16 h
  2. filtrationa solid filtered off
  3. customThe filtrate was evaporated to dryness
  4. customthe combined solids were purified by trituration with pentane

Sources & evidence

ORD record
ord-e3d6d064b90a48878abd7eaece13c34b
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

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