Water → N-(4-Bromopyridin-2-yl)acetamide

HRID 2359103Notes

Reaction equation

HRID 2359103 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=1.N1C=CC=CC=1.[C:15](Cl)(=[O:17])[CH3:16].O>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:15](=[O:17])[CH3:16])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 6367Acetyl chlorideHCID 6932822-Amino-4-bromopyridine

Product 1

HCID 59529635N-(4-Bromopyridin-2-yl)acetamideYield 72.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-bromo-2-aminopyridine (87 mmol) and pyridine (130 mol) in 200 mL dichloromethane was added dropwise acetyl chloride (117 mmol). The reaction mixture was stirred at room temperature for 4 h. Water was added and the reaction mixture was extracted with dichloromethane. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated. The residue was washed with hexane to afford 13.5 g of N-(4-bromopyridin-2-yl)acetamide (72% yield).

Workup

  1. extractionthe reaction mixture was extracted with dichloromethane
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. washThe residue was washed with hexane

Sources & evidence

ORD record
ord-689ebe405bc945caa7359d439380cff9
Source dataset
uspto-grants-2014_04
Patent number
US08685974B2

Reaction notes

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