2-Nitro-6-(trifluoromethoxy)aniline → 3-(Trifluoromethoxy)benzene-1,2-diamine

HRID 220272Notes

Reaction equation

HRID 220272 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][C:11]([F:14])([F:13])[F:12])[C:5]=1[NH2:15])([O-])=O>CCO>[F:12][C:11]([F:13])([F:14])[O:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([NH2:1])[C:5]=1[NH2:15]

Participants

3

Reactant 1

HCID 669159442-Nitro-6-(trifluoromethoxy)aniline

Product 1

HCID 140115773-(Trifluoromethoxy)benzene-1,2-diamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Trifluoromethoxy-benzene-1,2-diamine was synthesized by dissolving 0.79 g of 2-nitro-6-trifluoromethoxy-phenylamine (J. Med. Chem. 1999, 42, 15, 2828-2843) in 20 mL EtOH, evacuating 3 times with N2 and adding 80 mg of 10 wt % Pd/C. The reaction mixture was stirred under a H2 atmosphere (balloon) for 5 h. Filtration over a pad of celite and washing with EtOH and EtOAc yielded after concentration in vacuo 0.55 g of 3-trifluoromethoxy-benzene-1,2-diamine as brown oil.

Workup

  1. customevacuating 3 times with N2
  2. additionadding 80 mg of 10 wt % Pd/C
  3. filtrationFiltration over a pad of celite
  4. washwashing with EtOH and EtOAc
  5. customyielded
  6. concentrationafter concentration in vacuo 0.55 g of 3-trifluoromethoxy-benzene-1,2-diamine as brown oil

Sources & evidence

ORD record
ord-b0ed12d3e6784343a388d6b69fad23b9
Source dataset
uspto-grants-2012_06
Patent number
US08202885B2

Reaction notes

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