Acetic Acid → HCID 13682570, compound

Participants

Reaction Steps

In 5 ml of N,N-dimethylformamide was dissolved 0.7 g of methyl 5-(cyclopenten-1-yl)-2-(4-hydroxy-2-methylphenylaminomethylene)-3-oxo-4-pentenoate, and they were reacted at 140° C. for 2 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure, and the residue was purified by a column chromatography (Wako Silica Gel C-200; eluent: chloroform) to obtain an oily substance. This oily substance was dissolved in 10 ml of dioxane, and 0.5 g of 2,3,5,6-tetrachloro-p-benzoquinone was added thereto. They were reacted at 80° C. for 30 minutes. The reaction mixture was cooled to room temperature, and the precipitated crystals were collected by filtration, and washed with 5 ml of dioxane. These crystals were dissolved in a mixture of 5 ml of methanol and 5 ml of a 1N aqueous sodium hydroxide solution, the resulting mixture was subjected to reaction at room temperature for 30 minutes. The reaction mixture was adjusted to a pH of 5.5 with acetic acid and the precipitated crystals were collected by filtration, washed with water, and dried to obtain 1.3 g of 6-(cyclopenten-1-yl)-1-(4-hydroxy-2-methylphenyl)-4-oxo-1,4-dihydronicotinic acid having a melting point of 211°-213° C.

Provenance & Evidence