Ethyl Acetate → 3-Amino-5-(trifluoromethyl)picolinamide
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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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
- filtrationThe reaction mixture was filtered
- concentrationconcentrated
- 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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