Water → 4-Iodo-N-propyl-2-pyridone

HRID 1470721Notes

Reaction equation

HRID 1470721 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][NH:5][C:4](=[O:8])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].I[CH2:16][CH2:17][CH3:18].O>CN(C=O)C>[I:1][C:2]1[CH:7]=[CH:6][N:5]([CH2:16][CH2:17][CH3:18])[C:4](=[O:8])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 336431-IodopropaneHCID 205825354-Iodo-1,2-dihydropyridin-2-one

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2.0 g (9.05 mmol) 4-iodo-1H-pyridin-2-one and 3.13 g (22.6 mmol) potassium carbonate in 10 mL DMF are added 1.05 mL (10.9 mmol) 1-iodopropane. The mixture is stirred for 2 h at rt. Subsequently the mixture is poured into water and extracted with ethyl acetate (2×). The combined organic layers are washed with sat. NaHCO3-solution. After drying over sodium sulphate, the solvent is removed in vacuo and the residue is purified by HPLC (column: Agilent Stablebond C18, 7 μM; eluent A: water+0.15% HCOOH, eluent B: MeOH) to yield the desired product.

Workup

  1. extractionextracted with ethyl acetate (2×)
  2. washThe combined organic layers are washed with sat. NaHCO3-solution
  3. dry with materialAfter drying over sodium sulphate
  4. customthe solvent is removed in vacuo
  5. customthe residue is purified by HPLC (column: Agilent Stablebond C18, 7 μM; eluent A: water+0.15% HCOOH, eluent B: MeOH)

Sources & evidence

ORD record
ord-915e2b8f6f2c4308b19c8a24bf016596
Source dataset
uspto-grants-2015_04
Patent number
US09006450B2

Reaction notes

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