Hydroxyamine hydrochloride → 3-Trifluoromethyl-4-phenyl-5-aminoisoxazole
Reaction equation
Cl.[NH2:2][OH:3].[F:4][C:5]([F:18])([F:17])[C:6]([CH:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:9]#[N:10])=O>CO>[F:4][C:5]([F:18])([F:17])[C:6]1[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:9]([NH2:10])[O:3][N:2]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Methanol (53 ml) and 96% hydroxylamine hydrochloride (2.82 g, 0.0390 mole, 1.3 eq.) were added to -(trifluoroacetyl)phenylacetonitrile (6.96 g, 0.0300 mole) and the mixture was heated under reflux for 68 hours. After methanol was distilled off under reduced pressure and the resulting residue was neutralized with a 8% solution of sodium bicarbonate, the solution was extracted with methylene chloride. After being dried with anhydrous sodium sulfate, it was concentrated and purified by column chromatography on silica gel to give the title compound (5.62 g, 82.1%). The product was recrystallized from benzene-cyclohexane to recover the title compound (4.80 g, 70.1%) as pale yellow needles, m.p. 89°-91° C.