Chlorotrimethylsilane → Methyl 6-methyl-2-oxo-1,2-dihydropyridine-4-carboxylate

Participants

Reaction Steps

1,6-Dimethyl-2-oxo-1,2-dihydro-pyridine-4-carboxylic acid (1.0 g, 6.5 mmol) was suspended in dry methanol (8 mL) and chlorotrimethylsilane (2.8 g, 26 mmol) was added at room temperature. The reaction was stirred for 36 hours at room temperature. The solvent was removed under reduced pressure and the residue was dissolved in a mixture of dichloromethane/methanol (25 mL) and saturated aqueous sodium bicarbonate (25 mL) was added. A precipitate formed which was filtered off and washed with water and MTBE and air-dried. The filtrate was diluted with methanol/dichloromethane and water and the layers were separated. The aqueous layer was extracted once more with dichloromethane. The combined organic layers were dried (sodium sulfate), filtered and concentrated. Both the previously precipitated material and the concentrated organic layer consisted of product and were combined to afford of the title compound (820 mg, 75%).

Provenance & Evidence