《Syntheses of nitrogen-containing heterocycles. XXI. The preparation and reactions of some isoxazoles》 was published in Chemische Berichte in 1960. These research results belong to Dornow, Alfred; Treckenburg, Harald. SDS of cas: 29278-09-9 The article mentions the following:
The reaction of the enol ethers of BzCH(CN)2 and BzCH(CN)CO2Et with NH2OH yielded 5-aminoisoxazoles carrying a CN or CO2Et group, resp., in o-position to the amino group. NH2OH.HCl (1.6 g.) in 8.3 cc. 10% aqueous NaOH treated at 25° with 4.2 g. Ph(MeO)C:C(CN)2 (I) in small portions, stirred 3 hrs., filtered, and the residue dissolved in warm MeoH and reprecipitated with H2O gave 0.4 g. 5-amino-3-phenyl-4-cyanoisoxazole (II), prisms, m. 193°. NH2OH.HCl (0.56 g.) in 3.2 cc. 10% aqueous NaOH treated with stirring with 1.75 g. p-Cl derivative of I in small portions below 30°, stirred 3 hrs. and filtered, and the residue reprecipitated from MeOH with H2O gave 1.25 g. p-Cl derivative of II, m. 205°. NH2OH.HCl (0.35 g.) in 2 cc. 10% aqueous NaOH treated with stirring with 1 g. Ph(MeO)C:C(CN)2 (III) in small portions below 25°, stirred 3 hrs., and filtered gave 0.95 g. 4-CO2Et analog (IV) of I, m. 123°(MeOH). NH2OH.HCl (0.3 g.) in 2 cc. 10% aqueous NaOH treated with stirring with 1.5 g. p-NO2 derivative of III in small portions below 30°, stirred 3 hrs., and filtered yielded 1.2 g. p-NO2 derivative of IV, m. 208°(MeOH). IV (2.2 g.) added to 0.5 g. Na in 20 cc. EtOH, refluxed 3 hrs., evaporated, and the residue dissolved in H2O, acidified with dilute HCl, and filtered gave 1.55 g. 3-phenyl-4-cyano-5-isoxazolone (V), m. 195° (3:1 H2O-HCl). V (0.9 g.) in 20 cc. dry Et2O treated dropwise with cooling with CH2N2-Et2O, after the N evolution ceased treated with a small excess of CH2N2, evaporated, and the residue dried on a clay plate gave 0.7 g. 5-methoxy-3-phenyl-4-cyanoisoxazole (VI), m. 100° (50% aqueous MeOH). VI (0.5 g.) treated with 2.5 cc. piperidine and 2.5 cc. H2O, heated to solution, diluted with iced H2O, and filtered yielded 0.35 g. 5-piperidino analog of II, m. 84° (MeOH). VI (1 g.) and 0.5 g. H2NC(:NH)NH2.HCl added to 0.15 g. Na in 20 cc. absolute EtOH, refluxed 3 hrs., cooled, and filtered gave 0.75 g. 4,6-diamino-3-phenylisoxazolo[5,4-d]pyrimidine, m. 256° (glacial AcOH). In addition to this study using Ethyl 5-amino-3-phenylisoxazole-4-carboxylate, there are many other studies that have used Ethyl 5-amino-3-phenylisoxazole-4-carboxylate(cas: 29278-09-9SDS of cas: 29278-09-9) was used in this study.
Ethyl 5-amino-3-phenylisoxazole-4-carboxylate(cas: 29278-09-9) belongs to anime. Amines can be classified according to the nature and number of substituents on nitrogen. Aliphatic amines contain only H and alkyl substituents. Aromatic amines have the nitrogen atom connected to an aromatic ring.Important amines include amino acids, biogenic amines, trimethylamine, and aniline. Inorganic derivatives of ammonia are also called amines, such as monochloramine (NClH2).SDS of cas: 29278-09-9
Referemce:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem