5-Chloro-2-nitro-4-(trifluoromethoxy)aniline → 4-Chloro-5-(trifluoromethoxy)-1,2-benzenediamine

HRID 408738Notes

Reaction equation

HRID 408738 reaction equation
[Cl:1][C:2]1[C:3]([O:12][C:13]([F:16])([F:15])[F:14])=[CH:4][C:5]([N+:9]([O-])=O)=[C:6]([NH2:8])[CH:7]=1>CN(C=O)C.[Pt]>[Cl:1][C:2]1[CH:7]=[C:6]([NH2:8])[C:5]([NH2:9])=[CH:4][C:3]=1[O:12][C:13]([F:16])([F:14])[F:15]

Participants

4

Reactant 1

HCID 265966075-Chloro-2-nitro-4-(trifluoromethoxy)aniline

Product 1

HCID 669375074-Chloro-5-(trifluoromethoxy)-1,2-benzenediamine

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 6228DimethylformamideSolvent

Procedure

5-Chloro-2-nitro-4-trifluoromethoxy-phenylamine (180 g, 0.7 mol, 1.0 equiv.) was dissolved in dry DMF (1 L) and then 5% Pt/C containing 50.2% water (4.0 g) was added. The reaction solution was hydrogenated (50 psi) at room temperature for 16 hours. HPLC analysis indicated complete reaction. MS [M+H]+ found 225.2. The reaction solution was used on the next step without isolation.

Workup

  1. customat room temperature
  2. customfor 16 hours
  3. customreaction

Sources & evidence

ORD record
ord-be5fcd9e6bb34547861cdd15571dab2a
Source dataset
uspto-grants-2014_06
Patent number
US08759345B2

Reaction notes

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