1-Bromopropane → 4-Iodo-N-propyl-2-pyridone

HRID 76123Notes

Reaction equation

HRID 76123 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][NH:5][C:4](=[O:8])[CH:3]=1.Br[CH2:10][CH2:11][CH3:12].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[I:1][C:2]1[CH:7]=[CH:6][N:5]([CH2:10][CH2:11][CH3:12])[C:4](=[O:8])[CH:3]=1

Participants

5

Reactant 3

HCID 78401-BromopropaneHCID 11430Potassium CarbonateHCID 205825354-Iodo-1,2-dihydropyridin-2-one

Product 1

HCID 666349664-Iodo-N-propyl-2-pyridone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 2.0 g (9.05 mmol) 4-iodo-2-pyridone in 10 mL DMF are added 1.00 mL (10.9 mmol) 1-bromopropane and 3.13 g (22.6 mmol) K2CO3. The reaction mixture is stirred at r.t. over night. The reaction is quenched by the addition of water. The resulting mixture is extracted with EtOAc. The organic layer is washed with aq. NaHCO3 solution, dried with Na2SO4 and the solvent is removed in vacuo. The residue is purified by column chromatography (silica gel, heptane/EtOAc. 70/30→50/50)

Workup

  1. customThe reaction is quenched by the addition of water
  2. extractionThe resulting mixture is extracted with EtOAc
  3. washThe organic layer is washed with aq. NaHCO3 solution
  4. dry with materialdried with Na2SO4
  5. customthe solvent is removed in vacuo
  6. customThe residue is purified by column chromatography (silica gel, heptane/EtOAc. 70/30→50/50)

Sources & evidence

ORD record
ord-340f5c8ec0c6415aaee92d3faedb6a2e
Source dataset
uspto-grants-2014_09
Patent number
US08835472B2

Reaction notes

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