Ammonium Chloride → 5-Bromonicotinamide

HRID 1830888Notes

Reaction equation

HRID 1830888 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7](O)=[O:8].[Cl-].[NH4+].Cl.C([N:16]=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1>CN(C=O)C.O.C(OCC)(=O)C.C(N(CC)CC)C>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([NH2:16])=[O:8]

Participants

9

Reactant 4

HCID 25517Ammonium ChlorideHCID 887075-Bromonicotinic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 18085-BromonicotinamideYield 46.4%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-Bromonicotinic acid (5.05 g), ammonium chloride (2.10 g), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (7.30 g), 1-hydroxy-1H-benzotriazole monohydrate (3.90 g) and triethylamine (5.5 ml) were suspended in DMF (40 ml) and the mixture was stirred at room temperature for 16 hrs. Ethyl acetate and water were added to the reaction mixture and the organic layer was washed with saturated aqueous sodium hydrogen carbonate, water and saturated brine. The organic layer was concentrated by drying and recrystallized from ethyl acetate to give the title compound (2.33 g) as colorless needle crystals.

Workup

  1. washthe organic layer was washed with saturated aqueous sodium hydrogen carbonate, water and saturated brine
  2. concentrationThe organic layer was concentrated
  3. customby drying
  4. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-5d24d23ce20241e98c25ba5baf5cb16a
Source dataset
uspto-grants-2006_06
Patent number
US07067537B2

Reaction notes

Loading…