Methylamine → 4-Fluoro-2-nitro-N-methylaniline

HRID 422457Notes

Reaction equation

HRID 422457 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH3:12][NH2:13]>CCO.O>[F:8][C:5]1[CH:6]=[CH:7][C:2]([NH:13][CH3:12])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 677672,5-Difluoronitrobenzene

Product 1

HCID 27746624-Fluoro-2-nitro-N-methylanilineYield 99%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

1,4-Difluoro-2-nitrobenzene (2.63 g, 16.53 mmol) was dissolved in EtOH (9 mL) and Methylamine 40% in Water (9 mL) was added dropwise at 0° C. and the mixture was warming up to RT overnight 75 mL of water was added to the reaction mixture and the orange solid was filtered and washed with water (2*10 ml) to afford 2.78 g of 4-fluoro-N-methyl-2-nitrobenzenamine (Yield: 99%) as an orange crystalline solid.

Workup

  1. additionwas added to the reaction mixture
  2. filtrationthe orange solid was filtered
  3. washwashed with water (2*10 ml)

Sources & evidence

ORD record
ord-452c85e2dbcc4ccaa213b5e770fad40a
Source dataset
uspto-grants-2012_01
Patent number
US08101637B2

Reaction notes

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