2-Nitro-4-(trifluoromethoxy)aniline → 4-(Trifluoromethoxy)benzene-1,2-diamine

HRID 1982946Notes

Reaction equation

HRID 1982946 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([O:10][C:11]([F:14])([F:13])[F:12])[CH:7]=[CH:6][C:5]=1[NH2:15])([O-])=O>[Ni].CCO>[F:12][C:11]([F:13])([F:14])[O:10][C:8]1[CH:9]=[C:4]([NH2:1])[C:5]([NH2:15])=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 27757722-Nitro-4-(trifluoromethoxy)aniline

Product 1

HCID 27739594-(Trifluoromethoxy)benzene-1,2-diamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

2-nitro-4-trifluoromethoxy-phenylamine Compound 16a (0.5 g, 2.25 mmol) was dissolved into EtOH (30 mL) and Raney Ni (˜0.5 g, prewashed with EtOH) was added. The mixture was shaken in a Parr shaker under H2 (50 psi) at room temperature overnight, filtered through Celite and the solvent was evaporated to dryness to provide 4-trifluoromethoxy-benzene-1,2-diamine Compound 16b (0.373 g, yield 86%) as a red-brown semi-solid.

Workup

  1. additionwas added
  2. filtrationfiltered through Celite
  3. customthe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-c512a1b59d8f4595aa6bfa5e3f8b98a5
Source dataset
uspto-grants-2009_06
Patent number
US07541367B2

Reaction notes

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