Chlorotrimethylsilane → HCID 70984516, compound

Participants

Reaction Steps

To a stirred solution of 2-methylquinoline-8-carboxylic acid (0.830 g, 4.43 mmol) in MeOH (20 mL) was added dropwise chlorotrimethylsilane (2.41 g, 22.2 mmol). The reaction mixture was heated at reflux overnight. After cooling, the reaction was concentrated under reduced pressure. The residue was dissolved in water and basified by dropwise addition of saturated aqueous NaHCO3 solution. The mixture was extracted with EtOAc. The combined organic layers were washed with brine, dried and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (3:1 hexane/EtOAc) to give methyl 2-methylquinoline-8-carboxylate (0.290 g, 33%).

Provenance & Evidence