* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
With hydroxylamine; sodium hydroxide In water for 14 h; Inert atmosphere; Reflux
General procedure: Ketonitrile 5 (100 mmol) was added to 15percent aqueous NaOH solution(100 mL) followed by hydroxylamine (200 mmol). The resulting mixture was heated at reflux for 14 h, cooled down to r.t., theresulting precipitate was isolated by filtration and crystallized from isopropyl alcohol.
19.8%
With sodium hydroxide; hydroxyammonium sulfate In ethanol; water at 20 - 80℃; for 24 h;
Example 145; N-(3-Phenylisoxazol-5-yl)-4-(3-phenyl-1,2,4-thiadiazol-5-yl)piperazine-1-carboxamide; (1) 3-Phenylisoxazole-5-amine; A mixture of 3-oxo-3-phenylpropanenitrile (5.00 g, 34.4 mmol), hydroxylamine sulfate (3.10 g, 18.9 mmol), ethanol (35 ml) and an aqueous solution (35 ml) of sodium hydroxide (1.66 g, 41.4 mmol) was stirred at 80°C for 24 hours. After cooling to room temperature, the reaction mixture was adjusted to pH=11 by addition of an aqueous 8N sodium hydroxide solution and then extracted with chloroform. The extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (hexane : ethyl acetate = 1 : 1) to obtain the desired product (1.09 g, 19.8percent) as a solid. 1H-NMR (CDCl3) δ; 4.00 (2H, br s), 6.09 (1H, s), 7.41 - 7.46 (3H, m), 7.70 - 7.73 (2H, m).
Reference：
[1] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 6, p. 1914 - 1925
[2] Organic Letters, 2017, vol. 19, # 4, p. 934 - 937
[3] Organic Letters, 2018, vol. 20, # 9, p. 2774 - 2777
[4] Journal of Medicinal Chemistry, 2012, vol. 55, # 3, p. 1082 - 1105
[5] Patent: EP1813606, 2007, A1, . Location in patent: Page/Page column 81
[6] Justus Liebigs Annalen der Chemie, 1891, vol. 266, p. 329
[7] Heterocycles, 1991, vol. 32, # 6, p. 1153 - 1158
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Yield
Reaction Conditions
Operation in experiment
76%
With hydroxylamine hydrochloride; sodium hydroxide In ethanol at 20℃; for 12 h;
The mixture of 3-phenylpropiolonitrile (0.07 g, 0.5 mmol), sodium hydroxide (0.02 g, 0.5 mmol) and hydroxylamine hydrochloride (0.04 g, 0.5 mmol) in EtOH (6 mL) was stirred at room temperature for 12 h. The reaction was monitored by TLC. After the completion of the reaction, the mixture was extracted with ethyl acetate (3×10 mL), and the liquor was washed with saturated brine (3×10 mL). The resulting organic phase was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel to give product (0.06 g, 76percent). 3-Phenylisoxazol-5-amine (5a)7 White solid, m.p.: 110 – 111 °C. 1H NMR (600 MHz, CDCl3) δ 7.74 – 7.69 (m, 2H), 7.42 –7.40 (m, 3H), 5.43 (s, 1H), 4.53 (bs, 2H). 13C NMR (150 MHz, CDCl3) δ 168.80, 163.85, 129.72, 129.68, 128.69, 126.58, 78.25. Anal. Calcd. for C9H8N2O: C, 67.49; H, 5.03; N, 17.49. Found: C, 67.54; H, 5.01; N, 17.45.
Reference：
[1] Tetrahedron Letters, 2018, vol. 59, # 52, p. 4622 - 4625
[2] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1907, vol. 144, p. 1281[3] Bulletin de la Societe Chimique de France, 1907, vol. <4> 1, p. 1092,1093
Reference：
[1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1984, # 5, p. 1079 - 1083
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1984, # 5, p. 1079 - 1083
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Reference：
[1] Gazzetta Chimica Italiana, 1946, vol. 76, p. 148,163
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