HCID 178508561, compound → HCID 178522562, compound

Participants

Reaction Steps

6.3 g of 4-hydroxy-8-trifluoromethyl-quinoline-3-carboxylic acid chloride were added with stirring under an inert gas to 90 ml of pyridine and a solution of 2.35 g of 2-imino-2,3,4,5-tetrahydrothiazole in 15 ml of pyridine were added thereto. The mixture was stirred for 18 hours and was evaporated to dryness. The 11.5 g of residue were taken up in 40 ml of a 10% potassium carbonate solution and the solution was extracted with ethyl acetate. The combined organic phases were chromatographed over silica gel and the product was eluted with a 9-1 benzene-ethanol mixture. The elute was dried and the product was crystallized from ethanol to obtain 1.93 g of N-(4,5-dihydro-2-thiazolyl)-4-hydroxy-8-trifluoromethyl-quinoline-3-carboxamide melting at 267°-268° C.

Provenance & Evidence