1H-1,2,4-Triazole → HCID 70222247, compound

Participants

Reaction Steps

A mixture of intermediate 6 (8.4 g), 1,2,4-triazole (4.89 g) and potassium carbonate (9.78 g) in acetonitrile (300 ml) was stirred and refluxed for 12 hours. The solvent was evaporated and the residue was partitioned between CH2Cl2 and water. The separated organic layer was dried over MgSO4, filtered and the filtrate evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /CH3OH/NH4OH 98.5/1.5/0.1). The pure fractions were collected and the solvent evaporated. The residue was crystallized from diisopropyl ether/petrol ether, yielding 1.51 g (32%) (±)-5-chloro-6-[1H-1,2,4-triazol-1-yl[3-(trifluoromethyl)phenyl]-methyl]quinoline (intermediate 7; mp. 144.5° C.). In a similar manner, there were prepared: (±)-8-methyl-6-[1H-1,2,4-triazol-1-yl[3-(trifluoromethyl)phenyl]methyl]quinoline (intermediate 8; mp. 108.9° C.) and (±)-8-fluoro-6-[1H-1,2,4-triazol-1-yl[3-(trifluoromethyl) phenyl]methyl]quinoline (intermediate 9; mp. 146.6° C.).

Provenance & Evidence