HCID 23359035, compound → 2,4-Difluoro-3,6-dimethylaniline

HRID 232652Notes

Reaction equation

HRID 232652 reaction equation
[F:1][C:2]1[C:8]([CH3:9])=[C:7]([F:10])[CH:6]=[C:5]([CH2:11]SC)[C:3]=1[NH2:4]>[Ni].C(O)C>[F:1][C:2]1[C:8]([CH3:9])=[C:7]([F:10])[CH:6]=[C:5]([CH3:11])[C:3]=1[NH2:4]

Participants

4

Reactant 1

HCID 23359035HCID 23359035, compound

Product 1

HCID 233590392,4-Difluoro-3,6-dimethylanilineYield 84.8%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent2×

Procedure

To a solution of Raney nickel (50 g) in ethanol (100 ml) is added a solution of 2,4-difluoro-3-methyl-6-methylthiomethylaniline (4.79 g) in ethanol (30 ml) at room temperature with stirring, followed by stirring at room temperature for 30 minutes. The Raney nickel is filtered off and the filtrate is diluted with water, extracted with dichloromethane, and the extract is washed with water and dried. The solvent is distilled off under reduced pressure to give 2,4-difluoro-3,6-dimethylaniline (3.14 g).

Workup

  1. stirringby stirring at room temperature for 30 minutes
  2. filtrationThe Raney nickel is filtered off
  3. additionthe filtrate is diluted with water
  4. extractionextracted with dichloromethane
  5. washthe extract is washed with water
  6. customdried
  7. distillationThe solvent is distilled off under reduced pressure

Sources & evidence

ORD record
ord-30bbf59b6a494ba79d5c9790d1dd69ef
Source dataset
uspto-grants-1997_01
Patent number
US05591744

Reaction notes

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