Water → N-(4-bromopyridin-2-yl)propanamide

HRID 2359104Notes

Reaction equation

HRID 2359104 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:18])[CH2:16][CH3:17].O>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:15](=[O:18])[CH2:16][CH3:17])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 62324Propionyl chlorideHCID 6932822-Amino-4-bromopyridine

Product 1

HCID 67073822N-(4-bromopyridin-2-yl)propanamideYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-bromo-2-aminopyridine (580 mmol) in 1.5 L dichloromethane was added pyridine (1.16 mol). The mixture was stirred for 20 min. Propionyl chloride (669 mmol) was added dropwise. The reaction mixture was stirred at room temperature for 5 h. Water was added and the reaction mixture was extracted with dichloromethane. The combined organic layer was washed with brine, dried and concentrated. The residue was recrystallized from hexane/ethyl acetate (6:1) to afford 112 g of N-(4-bromopyridin-2-yl)propanamide (85% yield).

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 5 h
  2. extractionthe reaction mixture was extracted with dichloromethane
  3. washThe combined organic layer was washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was recrystallized from hexane/ethyl acetate (6:1)

Sources & evidence

ORD record
ord-ba76828b415e4a938f02d6a1a9605ec2
Source dataset
uspto-grants-2014_04
Patent number
US08685974B2

Reaction notes

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