Ethanol → HCID 178468540, compound

Participants

Reaction Steps

2-Hydroxy-7,7-dimethyl-6,7-dihydro-5H-cyclopenta[b]pyridine-3-carboxylic acid (11.0 g) was dissolved in ethanol (100 ml), sulfuric acid (3.4 ml) was added and the mixture was stirred with heating to reflux for 12 hr. The reaction mixture was concentrated under reduced pressure to a half volume, the residue was basified with 8 M aqueous sodium hydroxide solution, and the mixture was extracted with ethyl acetate. The extract was washed successively with 1 M aqueous sodium hydroxide solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, and the fraction eluted with ethyl acetate-hexane (50:50-85:15) was concentrated under reduced pressure to give the object compound (3.45 g).

Provenance & Evidence