Pyridine → HCID 20074920, compound

Participants

Reaction Steps

19.7 g (0.25 mol) of pyridine were dissolved in 335 ml of methylene chloride. 15.2 (152 mmol) of chromium trioxide were added in portions under an atmosphere of nitrogen at temperatures below 35° C., and the mixture was stirred for 30 minutes. 4.0 g (0.02 mol) of 2-(1-hydroxyethyl)-7,8-dihydro-6H-pyrazolo[4,5,1-ij]quinoline (obtained by reaction of 2-formyl-7,8-dihydro-6H-pyrazolo[4,5,1-ij]quinoline with 2.5 equivalent of methylmagnesium bromide), dissolved in 40 ml of methylene chloride were then added. The mixture was stirred for a few minutes, decanted and evaporated in vacuum. The residue was chromatographed over silicagel using methylene chloride/ethyl acetate (3/1) as a eluent. 3.5 g of the desired product were obtained after evaporation of the desired fractions. Melting point 101°-102° C.

Provenance & Evidence