Water → 2-Acetamido-5-bromopyridine

HRID 2120103Notes

Reaction equation

HRID 2120103 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[C:9](Cl)(=[O:11])[CH3:10].O>N1C=CC=CC=1>[C:9]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1)(=[O:11])[CH3:10]

Participants

5

Reactant 3

HCID 962WaterHCID 6367Acetyl chlorideHCID 706222-Amino-5-bromopyridine

Product 1

HCID 2930972-Acetamido-5-bromopyridineYield 85%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 29 ml of pyridine was dissolved 1 g of 2-amino-5-bromopyridine which was then acetylated through reaction with 0.61 ml of acetyl chloride at room temperature for 15 hours with stirring. Following the addition of water, the reaction mixture was extracted with ethyl acetate, and the organic layer thus obtained was washed with brine. Dehydration, filtration and concentration under vacuum of the organic layer provided a solid which was then recrystallized in ethanol and hexane to obtain the title compound. 1.06 g. Yield 85%.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. customthe organic layer thus obtained
  3. washwas washed with brine
  4. filtrationDehydration, filtration and concentration under vacuum of the organic layer
  5. customprovided a solid which
  6. customwas then recrystallized in ethanol

Sources & evidence

ORD record
ord-24d236d01ae64950970b90f4d845cb0f
Source dataset
uspto-grants-2004_02
Patent number
US06689779B2

Reaction notes

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