Methanol → 3-phenyl-4-(trifluoromethyl)-5-(7-vinyl-4,5-dihydro-2H-benzo[g] indazol-3-yl)isoxazole

Participants

Reaction Conditions

Reaction Steps

To 2-(3-phenyl-4-(trifluoromethyl)isoxazole-5-carbonyl)-6-vinyl-3,4-dihydronaphthalen-1(2H)-one (Preparation 22A, 0.25 g, 0.608 mmol) in a 50 mL round bottom flask was added methanol (2 mL) followed by hydrazine hydrate (0.040 mL, 0.790 mmol) at room temperature. Dioxane (2 mL) was added and the homogenous reaction mixture was heated at 90° C. for 1 h. The reaction mixture was stirred at room temperature for 14 h, concentrated under reduced pressure, azeotroped with methanol (2×10 mL, water bath heated to ˜60° C.) and kept under high vacuum for 15 min to yield 3-phenyl-4-(trifluoromethyl)-5-(7-vinyl-4,5-dihydro-2H-benzo[g]indazol-3-yl)isoxazole (0.24 g, 0.454 mmol, 74.6% yield) as a thick oil. LC/MS M+1=408.1.

Provenance & Evidence