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

HRID 2263547Notes

Reaction equation

HRID 2263547 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 60 F) 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-241834275908415387348184fa442198
Source dataset
uspto-grants-2010_12
Patent number
US07851634B2

Reaction notes

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