Sodium Carbonate → HCID 13506776, compound

Participants

Reaction Steps

A mixture of 10 g of 1,4,5,6,7,8-hexahydro-2-methyl-5-oxo-4-(2,3,4,5,6-pentafluorophenyl)-1,7-naphthyridine-3-carboxylic acid methyl ester, 5.6 g of 3-phenoxypropylbromide, 10 g of sodium carbonate and 175 ml of n-butanol was stirred and refluxed for 18 hours. The mixture was filtered and the filtrate was evaporated to dryness. The residue was dissolved in ethyl acetate and extracted with water. After drying over magnesium sulfate, the ethyl acetate was removed in vacuo. The residue was dissolved in methanol and saturated with hydrogen chloride. The solvent was evaporated in vacuo. The residue was dissolved in ethyl acetate and left at room temperature for 18 hours. The solid was separated and recrystallized from ethanolether. A second recrystallization from methanol afforded 2.8 g of the title compound as the hydrochloride salt, m.p. 205° C. dec.

Provenance & Evidence