Trifluoroacetic acid → 6-Aminopicolinonitrile

HRID 921717Notes

Reaction equation

HRID 921717 reaction equation
[C:1]([C:3]1[N:8]=[C:7]([NH:9]C(=O)OC(C)(C)C)[CH:6]=[CH:5][CH:4]=1)#[N:2].C(O)(C(F)(F)F)=O>ClCCl>[NH2:9][C:7]1[N:8]=[C:3]([C:1]#[N:2])[CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 76849200HCID 76849200, compound

Product 1

HCID 5642986-AminopicolinonitrileYield 106.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a round bottom flask charged with tert-butyl (6-cyanopyridin-2-yl)carbamate (0.5383 g, 2.455 mmol) in dichloromethane (9.82 ml) was added TFA (2.455 ml). The reaction mixture was stirred at room temperature 4 h. Excess TFA was removed in vacuo. The crude residue was taken up in methanol and free based using 2 parallel Phenomenex 5 g SCX columns. The columns were flushed with three column volumes methanol and three column volumes 3.5 N ammonia/methanol. The ammonia layers were concentrated in vacuo to provide 6-aminopicolinonitrile (0.312 g).

Workup

  1. customExcess TFA was removed in vacuo
  2. customThe columns were flushed with three column volumes methanol and three column volumes 3.5 N ammonia/methanol
  3. concentrationThe ammonia layers were concentrated in vacuo

Sources & evidence

ORD record
ord-d307d8d558c64aadbbefadc28555e023
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

Loading…