Water → 4-Iodo-N-propyl-2-pyridone

HRID 330829Notes

Reaction equation

HRID 330829 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+].O>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

6

Reactant 4

HCID 962WaterHCID 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

2.00 g (9.05 mmol) 4-iodo-2-pyridone (XXII.1) are added to 1.00 mL (10.9 mmol) 1-bromopropane and 3.13 g (22.6 mmol) K2CO3 in 10 mL DMF. The mixture is stirred at rt over night. After that time, water is added and the mixture is extracted with EtOAc. The organic layer is washed with aq. NaHCO3 solution, dried over sodium sulphate and the solvent is removed in vacuo. The residue is purified by RP-HPLC (water+0.15% FA, MeOH).

Workup

  1. extractionthe mixture is extracted with EtOAc
  2. washThe organic layer is washed with aq. NaHCO3 solution
  3. dry with materialdried over sodium sulphate
  4. customthe solvent is removed in vacuo
  5. customThe residue is purified by RP-HPLC (water+0.15% FA, MeOH)

Sources & evidence

ORD record
ord-273df454719b460babdd2d064a4b7bfa
Source dataset
uspto-grants-2014_11
Patent number
US08877754B2

Reaction notes

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