Ethyl Acetate → 3-Amino-5-(trifluoromethyl)picolinamide

HRID 925471Notes

Reaction equation

HRID 925471 reaction equation
[N+:1]([C:4]1[C:5]([C:14]#[N:15])=[N:6][CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)([O-])=O.CC[O:18]C(C)=O>[Pd]>[NH2:1][C:4]1[C:5]([C:14]([NH2:15])=[O:18])=[N:6][CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 453821473-Nitro-5-(trifluoromethyl)picolinonitrile

Product 1

HCID 867281563-Amino-5-(trifluoromethyl)picolinamide

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of 3-nitro-5-trifluoromethyl-pyridine-2-carbonitrile (1194 g, 5500 mmol) in EtOAc (12 l) was added 450 g Pd/C (10%) and hydrogenated (1.1 bar) at ambient temperature for 7 days. The reaction mixture was filtered and concentrated. The crude product was recrystallized from heptane/DCM to give 880 g of the desired product as a yellowish solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. customThe crude product was recrystallized from heptane/DCM

Sources & evidence

ORD record
ord-0f4f76d86ff04cb3be9f0804485c3329
Source dataset
uspto-grants-2016_03
Patent number
US09284284B2

Reaction notes

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