Sodium Phosphate, Dibasic → N-(5-bromo-2-pyridinyl)butanamide

HRID 486248Notes

Reaction equation

HRID 486248 reaction equation
[C:1]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1)(=[O:5])[CH2:2][CH2:3][CH3:4].P([O-])([O-])(O)=O.[Na+].[Na+].[Br:20]Br>O.C(O)(=O)C>[C:1]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([Br:20])=[CH:9][N:8]=1)(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 24203Sodium Phosphate, DibasicHCID 24408BromineHCID 4606103HCID 4606103, compound

Product 1

HCID 876084N-(5-bromo-2-pyridinyl)butanamideYield 89.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To 53.6 g of an aqueous solution containing 0.2 mol of 2-butanamido pyridine (If), a solution containing 71 g (0.5 mol) of disodium hydrogenphosphate dissolved in 490 g of water was added. To this mixture, a solution containing 54.2 g (0.34 mol) of bromine dissolved in 54 g of acetic acid was added with stirring at 10°-17° C. for 5 hours. After having been stirred at room temperature for one hour and then at 60° C. for one hour, the mixture was cooled. The crystal precipitated thereby was filtered. After the crystal was washed with water and dried, 43.7 g (yield: 89.8%) of 2-butanamido-5-bromopyridine (IIf) was obtained as a pale brown crystal.

Workup

  1. additionwas added
  2. additionwas added
  3. stirringAfter having been stirred at room temperature for one hour
  4. waitat 60° C. for one hour
  5. temperaturethe mixture was cooled
  6. customThe crystal precipitated
  7. filtrationthereby was filtered
  8. washAfter the crystal was washed with water
  9. customdried

Sources & evidence

ORD record
ord-e39c99c5cb9548c39b36d4ac355679e8
Source dataset
uspto-grants-1994_03
Patent number
US05290943

Reaction notes

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