4-Hydroxymethylpyridine → 8-methyl-6-[4-(4-pyridylmethoxy)phenyl]-2-(1H)-quinolone

Participants

Reaction Steps

A solution of diethylazodicarboxylate (0.189 cm3) in THF (5 cm3) was added at room temperature to a stirred suspension of 8-methyl-6-[4-hydroxyphenyl]-2-(1H)-quinolone (0.25 g), 4-hydroxymethylpyridine (0.109 g) and triphenylphosphine (0.315 g) in THF (10 cm3) under nitrogen. The mixture was heated under reflux for 18 hours, silica (10 g) (Merck "MK 60.9385" [Trade Mark]) was added and voltatile material was removed in vacuo. The residue was placed on top of a silica column (Merck "MK 60.9385" [Trade Mark]) and eluted with ethyl acetate:methanol, 9:1. Combination and evaporation of the appropriate fractions in vacuo gave a solid (0.24 g) which was recrystallised from ethyl acetate-methanol to afford the title compound, m.p. 270.5°-273.5°, (0.08 g).

Provenance & Evidence