2(1H)-Pyridinone, 1,3-dimethyl- synthesis
- Product Name:2(1H)-Pyridinone, 1,3-dimethyl-
- CAS Number:6456-92-4
- Molecular formula:C7H9NO
- Molecular Weight:123.15
Yield:6456-92-4 91%
Reaction Conditions:
Stage #1: 3-Methyl-1H-pyridin-2-onewith potassium tert-butylate in 1,4-dioxane at 100; for 2 h;Schlenk technique;Inert atmosphere;
Stage #2: methyl iodide in 1,4-dioxane at 80; for 16 h;Schlenk technique;Inert atmosphere;
Steps:
General procedure: In a dry Schlenk tube 6-methyl-2(1H)-pyridone (1) (3.43 g, 31.44 mmol) was dissolved in 50 mLof 1,4-dioxane and KOt-Bu (8.69 g, 62.88 mmol) was added. The mixture was stirred at 100 °C for 2 h, then cooled down to rt, MeI (19.6 mL, 314.41 mmol) was added dropwise and the mixture was stirred at 80 °C for 16 h. The solvent was removed under reduced pressure and the residue was separated between DCM and water. The extraction was performed using DCM (3×) and the combined organic phases were dried over MgSO4, filtered and evaporated. The residue was transferred to a column chromatography (5% MeOH in DCM) to afford 3a (orange solid), 3.70 g (96%).
References:
Wysocki, Jedrzej;Schlepphorst, Christoph;Glorius, Frank [Synlett,2015,vol. 26,# 11,art. no. ST-2015-B0171-L,p. 1557 - 1562] Location in patent:supporting information
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