Methyl iodide → 3-(benzyloxy)-1-methyl-1H-pyridin-2-one

HRID 1398521

Reaction equation

HRID 1398521 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([OH:15])=[N:11][CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].[CH3:18]I>CS(C)=O>[CH2:1]([O:8][C:9]1[C:10](=[O:15])[N:11]([CH3:18])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 178517714HCID 178517714, compound

Product 1

HCID 681815923-(benzyloxy)-1-methyl-1H-pyridin-2-oneYield 94.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 3-(benzyloxy)pyridin-2-ol (25 g, 123.00 mmol) and potassium hydroxide (10 g, 178.22 mmol, 1.45 equiv) in dimethylsulfoxide (250 mL) maintained under nitrogen atmosphere was added methyl iodide (27 g, 190.14 mmol) dropwise with stirring. The resulting solution was stirred overnight at room temperature then concentrated under vacuum. The residue was diluted with water (500 mL) then extracted with dichloromethane (2×400 mL). The combined organic layer was washed with water (3×500 mL), dried over anhydrous sodium sulfate and concentrated under vacuum to give the title compound (25 g, 93%) as a light brown oil: 1H NMR (400 MHz, DMSO) delta 7.44-7.32 (m, 5H), 7.29-7.27 (m, 1H), 6.91-6.88 (m, 1H), 6.12-6.09 (m, 1H), 5.02 (s, 2H), 3.44 (s, 3H).

Workup

  1. stirringThe resulting solution was stirred overnight at room temperature
  2. concentrationthen concentrated under vacuum
  3. additionThe residue was diluted with water (500 mL)
  4. extractionthen extracted with dichloromethane (2×400 mL)
  5. washThe combined organic layer was washed with water (3×500 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-d333884211c943c4b409461f90bad9cb
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Linked notes

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