3-Nitro-5-(trifluoromethyl)pyridin-2-amine → 5-(Trifluoromethyl)pyridine-2,3-diamine

HRID 908256Notes

Reaction equation

HRID 908256 reaction equation
[N+:1]([C:4]1[C:5]([NH2:14])=[N:6][CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)([O-])=O>[Ni].CO>[F:13][C:10]([F:11])([F:12])[C:8]1[CH:9]=[C:4]([NH2:1])[C:5]([NH2:14])=[N:6][CH:7]=1

Participants

4

Reactant 1

HCID 106083913-Nitro-5-(trifluoromethyl)pyridin-2-amine

Product 1

HCID 102144255-(Trifluoromethyl)pyridine-2,3-diamineYield 78.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a methanol 5 mL solution of 3-nitro-5-(trifluoromethyl)pyridin-2-amine (680 mg, 3.28 mmol) was added Raney nickel (240 mg charged as a wet slurry, washed 3× with 10 mL of H2O). The mixture was hydrogenated in a Parr shaker at 50 psi at room temperature for 1 hr, purged with N2 and filtered through a pad of celite. The celite pad was washed with methanol (5 mL×3). The filtrate was concentrated under reduced pressure to give the title compound (454 mg). LC/MS: m/z 178(M+H).

Workup

  1. additioncharged as a wet slurry
  2. washwashed 3× with 10 mL of H2O)
  3. custompurged with N2
  4. filtrationfiltered through a pad of celite
  5. washThe celite pad was washed with methanol (5 mL×3)
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a361ca31756b4141859dc1fb9a7c3e14
Source dataset
uspto-grants-2011_09
Patent number
US08017605B2

Reaction notes

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