Water → 3,5-Difluoro-N-methyl-2-nitroaniline

HRID 334727Notes

Reaction equation

HRID 334727 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4](F)[C:3]=1[N+:10]([O-:12])=[O:11].[CH3:13][NH2:14].O>CCO>[F:1][C:2]1[C:3]([N+:10]([O-:12])=[O:11])=[C:4]([NH:14][CH3:13])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

5

Reactant 3

HCID 962Water2×HCID 6329Methylamine3×HCID 675671,3,5-Trifluoro-2-nitrobenzene

Product 1

HCID 665982623,5-Difluoro-N-methyl-2-nitroanilineYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1,3,5-Trifluoro-2-nitrobenzene (3.0 g, 16.90 mmol) was dissolved in EtOH (29.7 mL) and Methylamine 40% in Water (1.44 mL, 17.80 mmol) was added dropwise at 0° C. The color went from bright yellow to an orange precipitate within 20 min. After 4 h at RT. 0.66 mL of Methylamine was added (9 mmol). To complete the reaction, an additional 0.26 ml (3.6 mmol) of Methylamine was added after 2 h at RT. The completion was achieved within 20 min. Water (75 mL) was added to the reaction mixture and the solid was isolated by filtration, washed with water (2*10 mL) and dried over high vacuum to afford 2.64 g of 3,5-difluoro-N-methyl-2-nitrobenzenamine (Yield: 83%) as an orange solid.

Workup

  1. customwithin 20 min
  2. customthe reaction
  3. waitThe completion was achieved within 20 min
  4. customthe solid was isolated by filtration
  5. washwashed with water (2*10 mL)
  6. customdried over high vacuum

Sources & evidence

ORD record
ord-e7cba5829f8c49a9a3176bff8508c6a2
Source dataset
uspto-grants-2014_11
Patent number
US08883826B2

Reaction notes

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