Sodium Hydroxide → 5-bromo-3-(3-methoxypropoxy)-1H-pyridin-2-one

HRID 252363Notes

Reaction equation

HRID 252363 reaction equation
[OH-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([OH:11])[C:7](=[O:10])[NH:8][CH:9]=1.I[CH2:13][CH2:14][CH2:15][O:16][CH3:17]>C(O)(=O)C>[Br:3][C:4]1[CH:5]=[C:6]([O:11][CH2:13][CH2:14][CH2:15][O:16][CH3:17])[C:7](=[O:10])[NH:8][CH:9]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 125630835-Bromopyridine-2,3-diolHCID 135229891-Iodo-3-methoxypropane

Product 1

HCID 231494755-bromo-3-(3-methoxypropoxy)-1H-pyridin-2-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a 1.4M NaOH solution at 0° C. are added 0.9 mol 5-bromo-3-hydroxy-1H-pyridin-2-one [34206-49-0]. The mixture is allowed to stir for 15 minutes and 0.9 mmol 1-iodo-3-methoxypropane [61542-10-7] are added carefully at 0° C. The mixture is stirred at room temperature for 3 hours, then neutralized with acetic acid to pH 7. The mixture is extracted with chloroform (10×) and the organic layer is dried over sodium sulphate, filtered and concentrated. The title compound is obtained from the residue by means of flash chromatography (SiO2 60F) and identified based on its Rf value.

Workup

  1. stirringThe mixture is stirred at room temperature for 3 hours
  2. extractionThe mixture is extracted with chloroform (10×)
  3. dry with materialthe organic layer is dried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-906cddcac298485ea485c8f0b863acf3
Source dataset
uspto-grants-2011_01
Patent number
US07868036B2

Reaction notes

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