Acetylenic compounds, XLIV. Synthesis of 3-aminoisoxazoles and 3-hydroxyisoxazoles (3-isoxazolones) was written by Iwai, Issei;Nakamura, Norio. And the article was included in Chemical & Pharmaceutical Bulletin in 1966.Recommanded Product: 14678-05-8 This article mentions the following:
A solution of β,4-dibromocinnamonitrile (0.0028 mole) in 10 ml. EtOH was mixed with NH2OH.HCl (0.016 mole) in 10 ml. 10% NaOH. After standing overnight, the mixture was extracted with ether. The ethereal layer was extracted with 10% HCl solution After neutralization with aqueous NaOH, yellow precipitate was taken up in ether. After evaporation of the solvent, the residue was crystallized from aqueous MeOH to yield 57% yellow 3-amino-5-(p-bromophenyl)isoxazole (I), m. 147-9°. To a solution of 12.2 g. ClCN in 150 ml. absolute ether was added a solution of Grignard reagent prepared from p-methoxyphenylpropiolonitrile (II), m. 78.5-80°. To a mixture of 0.018 mole NH2OH.HCl and 0.062 mole 10% NaOH was added a solution of 0.006 mole (II) in 25 ml. EtOH. After standing overnight the mixture was extracted with ether to give 41% 3-amino-5-(p-methoxyphenyl)isoxazole (III), m. 171-2°. Similarly prepared was 3-methyl-5-aminoisoxazole (IV) m. 84-5°, 3:1 mixture of 3-amino-5-phenylisoxazole and IV, 3-sulfanilamido-5-methylisoxazole, m. 166-7°, 5-aminoisoxazole, m. 75-7°, 5-benzamidoisoxazole, m. 134-5° (62% yield), 3 aminoisoxazole, b. 75-6°, 3-benzamidoisoxazole, m. 148-9°, 3-acetylsulfanilamidoisoxazole, m. 245-7° (decomposition), 3-sulfanilamidoisoxazole, m. 124-6°, 3-hydroxy-5-phenylisoxazole, m. 163-5°, 3-hydroxy-5-(p-nitrophenyl)isoxazole, m. 232-4° (decomposition), 3-hydroxy-5-(p-chlorophenyl)isoxazole, m. 220-1° (decomposition), 3-hydroxy-5-(p-methoxyphenyl)isoxazole, m. 212-14° (decomposition), 3-hydroxy-5-methylisoxazole, m. 84-5°, 3-hydroxyisoxazole, m. 98-9°, 3-phenyl-5-isoxazolone, m. 151-2°. In the experiment, the researchers used many compounds, for example, Isoxazol-5-amine (cas: 14678-05-8Recommanded Product: 14678-05-8).
Isoxazol-5-amine (cas: 14678-05-8) belongs to isoxazole derivatives. Isoxazoles present in various natural products and synthetic compounds of biological importance like antibacterial, antagonists, antiinflammatory, analgesics, and also show the applications in functional materials. Some alternative routes for the synthesis of isoxazoles have also been developed and reported. The 2-benzoyl-2-halo-2H-azirines provide 4-haloisoxazoles in good yields after heating in toluene at reflux temperature.Recommanded Product: 14678-05-8
Referemce:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem