2-Methylthiomethyl-3,4,6-trifluoroaniline → 3,4,6-Trifluoro-2-methylaniline

HRID 2394936Notes

Reaction equation

HRID 2394936 reaction equation
CS[CH2:3][C:4]1[C:10]([F:11])=[C:9]([F:12])[CH:8]=[C:7]([F:13])[C:5]=1[NH2:6]>[Ni].C(O)C>[CH3:3][C:4]1[C:10]([F:11])=[C:9]([F:12])[CH:8]=[C:7]([F:13])[C:5]=1[NH2:6]

Participants

4

Reactant 1

HCID 189744612-Methylthiomethyl-3,4,6-trifluoroaniline

Product 1

HCID 226251783,4,6-Trifluoro-2-methylanilineYield 71.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To 2-methylthiomethyl-3,4,6-trifluoroaniline (22.2 g) are added ethanol (400 ml) and Raney nickel (200 g) and the mixture is stirred at room temperature for 30 minutes. After the catalyst is filtered off, the filtrate is added with water and extracted with dichloromethane. The is dried over magnesium sulfate and concentrated to give 2-methyl-3,4,6-trifluoroaniline (12.3 g).

Workup

  1. filtrationAfter the catalyst is filtered off
  2. additionthe filtrate is added with water
  3. extractionextracted with dichloromethane
  4. dry with materialThe is dried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-af6c71ca824248268d9483ce199fcbe5
Source dataset
uspto-grants-1998_09
Patent number
US05811576

Reaction notes

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