Potassium Carbonate → 2-Amino-5-bromo-6-(2-furyl)nicotinonitrile

HRID 353216Notes

Reaction equation

HRID 353216 reaction equation
[Br:1]N1C(=O)CCC1=O.[NH2:9][C:10]1[N:17]=[C:16]([C:18]2[O:19][CH:20]=[CH:21][CH:22]=2)[CH:15]=[CH:14][C:11]=1[C:12]#[N:13].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[NH2:9][C:10]1[N:17]=[C:16]([C:18]2[O:19][CH:20]=[CH:21][CH:22]=2)[C:15]([Br:1])=[CH:14][C:11]=1[C:12]#[N:13]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 67184N-bromobutanimideHCID 103523832-Amino-6-(2-furyl)nicotinonitrile

Product 1

HCID 129921342-Amino-5-bromo-6-(2-furyl)nicotinonitrileYield 58.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-Bromosuccinimide (3.5 g, 19.7 mmol) was added to a solution (60 ml) of 2-amino-6-(2-furyl)nicotinonitrile (4.0 g, 21.6 mmol) in N,N-dimethylformamide in a nitrogen atmosphere at 1 to 2° C., followed by stirring as it was. After 30 minutes, the reaction solution was diluted with ethyl acetate and an aqueous saturated solution of potassium carbonate. The organic layer was washed with an aqueous saturated solution of potassium carbonate and an aqueous saturated solution of ammonium chloride, then dried over anhydrous sodium sulfate and concentrated. Methanol was added to the residue, and the resulting solid was collected by filtration and washed with methanol, to give the title compound (3.02 g, 53%) as a brown solid.

Workup

  1. washThe organic layer was washed with an aqueous saturated solution of potassium carbonate
  2. dry with materialan aqueous saturated solution of ammonium chloride, then dried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. additionMethanol was added to the residue
  5. filtrationthe resulting solid was collected by filtration
  6. washwashed with methanol

Sources & evidence

ORD record
ord-3a3728fee44d4a19b314b644e028e5a1
Source dataset
uspto-grants-2004_06
Patent number
US06750232B2

Reaction notes

Loading…