Hydrochloric Acid → HCID 18008969, compound

Participants

Reaction Steps

3-fluoro-2-naphthylamine (1.38 g, 8.57 mmol, see Step 2, Example 3) was placed in 20 mL concentrate HCl. The slurry was stirred in ice bath. To it was added dropwise a chilled solution of sodium nitrite (0.71 g, 10.3 mmol) in 4 mL water. After completion, the mixture was stirred for 30 min in ice bath. A chilled solution of SnCl2.2H2O (4.9 g, 21.6 mmol) in 4 mL concentrate HCl was added dropwise. The mixture was stirred for 30 min. It was chilled and filtered with a Buchner funnel to collect the solid hydrazine. The solid was dried in vacuuo. It was then dissolved in 50 mL glacial acetic acid. To it was added 4,4,4-trifluoro-1-(2-furyl)-1,3-butanedione (2.18 g, 10.6 mmol). The mixture was refluxed for 2 hrs. The solvent was removed in vacuuo. The residue was taken into DCM. It was washed with water ×2, dried, concentrated and subjected to flash column to isolate 3-trifluoromethyl-1-(3-fluoro-2-naphthyl)-5-(2-furyl)-1H-pyrazole (60%). Rf 0.52 (1:4 EtOAc:hexane). ES-MS: (M+H)+347.

Provenance & Evidence