(2-Chloro-6-nitro-4-trifluoromethylphenyl)-methylamine → 3-Chloro-N2-methyl-5-(trifluoromethyl)-1,2-benzenediamine

HRID 533666Notes

Reaction equation

HRID 533666 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([N+:12]([O-])=O)[C:3]=1[NH:15][CH3:16].[H][H]>[Ni].C(O)C>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([NH2:12])[C:3]=1[NH:15][CH3:16]

Participants

5

Reactant 2

HCID 67981579(2-Chloro-6-nitro-4-trifluoromethylphenyl)-methylamineHCID 178418361HCID 178418361, compound

Product 1

HCID 680910673-Chloro-N2-methyl-5-(trifluoromethyl)-1,2-benzenediamineYield 90.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a mixture of (2-chloro-6-nitro-4-trifluoromethylphenyl)-methylamine (3.70 g) and ethanol (60 ml), Raney® nickel (slurry in water, 0.5 ml) was added, and stirred under about 1 atm of hydrogen at room temperature for 1.5 hours. The reaction mixture was filtered. The filtrate was concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 2.95 g of 3-chloro-N2-methyl-5-trifluoromethylbenzene-1,2-diamine.

Workup

  1. additionwas added
  2. filtrationThe reaction mixture was filtered
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ef0cd4d1714d4f2c8a4006a157f61b7a
Source dataset
uspto-grants-2014_10
Patent number
US08853238B2

Reaction notes

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