Dimethylformamide → 5-Bromonicotinamide

HRID 1748657Notes

Reaction equation

HRID 1748657 reaction equation
C(Cl)(=O)C(Cl)=O.C[N:8](C)[CH:9]=[O:10].[Br:12][C:13]1[CH:14]=[C:15](C(O)=O)[CH:16]=[N:17][CH:18]=1>ClCCl>[Br:12][C:13]1[CH:14]=[C:15]([C:9]([NH2:8])=[O:10])[CH:16]=[N:17][CH:18]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 887075-Bromonicotinic acid

Product 1

HCID 18085-Bromonicotinamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (1.33 ml) and N,N-dimethylformamide (catalytic amounts) were added dropwise under ice-cooling to a solution of 5-bromopyridine-3-carboxylic acid (2.02 g) in dichloromethane, and stirred for an hour. The solvent was evaporated in a evaporator, the residue was dissolved in tetrahydrofuran (10 ml), to which ammonia water (28%; 1 ml) was added dropwise under ice-cooling, and stirred at room temperature for 0.5 hours. After completion of the reaction, water was added to the reaction mixture and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and concentrated. The residue was purified with column chromatography to give 5-bromopyridine-3-carboxamide (734 mg).

Workup

  1. customThe solvent was evaporated in a evaporator
  2. dissolutionthe residue was dissolved in tetrahydrofuran (10 ml), to which ammonia water (28%; 1 ml)
  3. additionwas added dropwise under ice-
  4. temperaturecooling
  5. stirringstirred at room temperature for 0.5 hours
  6. customAfter completion of the reaction, water
  7. additionwas added to the reaction mixture
  8. extractionextracted with ethyl acetate
  9. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  10. concentrationconcentrated
  11. customThe residue was purified with column chromatography

Sources & evidence

ORD record
ord-d893269e84374b08828f939bbf7c1c25
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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