3-Nitro-5-(trifluoromethyl)picolinamide → 3-Amino-5-(trifluoromethyl)picolinamide

HRID 627720Notes

Reaction equation

HRID 627720 reaction equation
[N+:1]([C:4]1[C:5]([C:14]([NH2:16])=[O:15])=[N:6][CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)([O-])=O>[Pd]>[NH2:1][C:4]1[C:5]([C:14]([NH2:16])=[O:15])=[N:6][CH:7]=[C:8]([C:10]([F:13])([F:11])[F:12])[CH:9]=1

Participants

3

Reactant 1

HCID 867281553-Nitro-5-(trifluoromethyl)picolinamide

Product 1

HCID 867281563-Amino-5-(trifluoromethyl)picolinamideYield 97%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A round bottom flask was charged with 3-nitro-5-(trifluoromethyl)picolinamide (850 mg, 3.62 mmol) and wet 5 wt. % Pd/C (769 mg, 0.362 mmol) and was purged with nitrogen. EtOAc (7230 μl) and then MeOH (7230 μl) were added, and the flask was evacuated and filled with hydrogen. The reaction was stirred at RT under hydrogen atmosphere for 17 h. The mixture was filtered through Celite and washed with EtOAc and MeOH. The filtrate was concentrated to provide 3-amino-5-(trifluoromethyl)picolinamide (720 mg, 3.51 mmol, 97% yield) as a white solid. LC/MS (ESI+) m/z=206.1 (M+H).

Workup

  1. customwas purged with nitrogen
  2. additionEtOAc (7230 μl) and then MeOH (7230 μl) were added
  3. customthe flask was evacuated
  4. additionfilled with hydrogen
  5. filtrationThe mixture was filtered through Celite
  6. washwashed with EtOAc and MeOH
  7. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-35eb8daf8fd0461188c01d3cf7f12c9d
Source dataset
uspto-grants-2016_04
Patent number
US09309263B2

Reaction notes

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