alpha-(2,2,2-Trifluoroacetyl)benzeneacetonitrile → 5-Trifluoromethyl-4-phenyl-3-aminoisoxazole

HRID 2291699Notes

Reaction equation

HRID 2291699 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]([CH:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:6]#[N:7])=[O:4].FC(F)(F)C1C(C2C=CC=CC=2)=C(N)O[N:19]=1>>[F:1][C:2]([F:14])([F:15])[C:3]1[O:4][N:7]=[C:6]([NH2:19])[C:5]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

3

Reactant 2

HCID 2776431alpha-(2,2,2-Trifluoroacetyl)benzeneacetonitrileHCID 156138913-Trifluoromethyl-4-phenyl-5-aminoisoxazole

Product 1

HCID 156138925-Trifluoromethyl-4-phenyl-3-aminoisoxazoleYield 83.2%

Procedure

A crude product was obtained according to the same procedure as described in Example 1 except that α-(trifluoroacetyl)phenylacetonitrile (23.12 g, 0.10 mole) was used. Crude yield: 3.69 g (16.2%). According to the measurement of NMR, it was found that this compound contained 83.2% of the title compound and 11.8% of 3-trifluoromethyl-4-phenyl-5-aminoisoxazole. The crude product was purified by column chromatography on silica gel as described in Example 1 to give the title compound (3.06 g, 13.4%) as colorless crystals, m.p. 91.5°-92.0° C.

Sources & evidence

ORD record
ord-05ed5681e2f449ae9e50059a404cb53d
Source dataset
uspto-grants-1989_01
Patent number
US04797492

Reaction notes

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