Ethanol → Trifluoromethyl toluidine

HRID 1707165Notes

Reaction equation

HRID 1707165 reaction equation
[NH2:1][C:2]1[C:3]([CH2:13]SC)=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:6][C:7]=1Cl.C(O)C>[OH-].[K+].[Ni]>[NH2:1][C:2]1[C:3]([CH3:13])=[C:4]([C:9]([F:10])([F:11])[F:12])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 233529853-Amino-4-chloro-2-methylthiomethylbenzotrifluoride

Product 1

HCID 2735932Trifluoromethyl toluidine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 14797Potassium HydroxideSolvent

Conditions

Temperature
70 °C

Procedure

Dissolve 2 g. of 3-amino-4-chloro-2-methylthiomethylbenzotrifluoride in 50 ml. of 90% ethanol which is 1 N in potassium hydroxide. Add 2 teaspoonfuls of Raney nickel (W-2). Stir at 70° C. for 3 hours, cool and filter. Add 50 ml. of water and extract three times with hexane. Dry and evaporate the combined organic extracts to yield the title compound.

Workup

  1. dissolutionDissolve 2 g
  2. temperaturecool
  3. filtrationfilter
  4. additionAdd 50 ml
  5. extractionof water and extract three times with hexane
  6. customDry
  7. customevaporate the combined organic extracts

Sources & evidence

ORD record
ord-301fc8bacd3f481283b5699e8652ac61
Source dataset
uspto-grants-1980_06
Patent number
US04209464

Reaction notes

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