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

HRID 2190508Notes

Reaction equation

HRID 2190508 reaction equation
F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH3:12][NH2:13]>O>[F:8][C:6]1[CH:5]=[CH:4][C:3]([N+:9]([O-:11])=[O:10])=[C:2]([CH:7]=1)[NH:13][CH3:12]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 679672,4-Difluoronitrobenzene

Product 1

HCID 229057745-fluoro-N-methyl-2-nitroanilineYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2,4-Difluoro-1-nitrobenzene (25.0 g, 157 mmol) was stirred and thereto was added dropwise 40% aqueous methylamine solution (38.4 g) at 0° C. over not less than 15 min. After the completion of the dropwise addition, the mixture was continuously stirred at the same temperature for 1.5 hr. Water (500 mL) was added to the reaction mixture, and the resulting solid was collected by filtration to give the title compound (26.4 g, 99%) as yellow crystals.

Workup

  1. additionAfter the completion of the dropwise addition
  2. filtrationthe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-471c384b566b46ec80bfc7ec0c0bb0b0
Source dataset
uspto-grants-2012_12
Patent number
US08324395B2

Reaction notes

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