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

HRID 1526638Notes

Reaction equation

HRID 1526638 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 (72300 and then MeOH (72300 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 (72300 and then MeOH (72300 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-1a69262c1a5f4a64a08315a5bc276c0b
Source dataset
uspto-grants-2015_07
Patent number
US09085576B2

Reaction notes

Loading…