Water → HCID 21186679, compound

Participants

Reaction Steps

Ethyl methyl-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carboxylate (2.50 g, 10.1 mmol) was dissolved in acetic acid (7.0 ml), the solution was mixed with concentrated sulfuric acid (1.4 ml), and then 11% acetic acid aqueous solution (4.8 ml) of chromic anhydride (1.41 g, 14.1 mmol) was added thereto at 10 to 15° C. spending about 1 hour. After 6 hours of stirring at room temperature, water was added to the reaction solution to which was subsequently added dropwise 2-propanol at 0° C. to decompose excess chromic acid. The solvent was evaporated under reduced pressure, the thus obtained residue was neutralized with 20% sodium hydroxide aqueous solution at 0° C. and mixed with chloroform, and then the insoluble matter was removed by celite filtration and washed with chloroform. The resulting filtrate was extracted with chloroform, washed with water and saturated brine in that order and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (ether:hexane=1:1) to obtain the title compound (284.7 mg, 10.8%) as colorless oil.

Provenance & Evidence