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

HRID 1271

Reaction equation

HRID 1271 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-6ef792f7c5b74d278abb8630ab09df7e
Source dataset
uspto-grants-1998_03
Patent number
US05723648

Linked notes

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