β-Aminovinyl ketones. II. Some reactions of alkyl 2-dialkylaminovinyl ketones was written by Kochetkov, N. K.. And the article was included in Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya in 1954.Safety of 5-Methylisoxazole This article mentions the following:
AcCH:CHNEt2 (I) (5 g.) in 40 ml. EtOH hydrogenated over 0.15 g. PtO2 11 hrs. at room temperature absorbed only 750 ml. H; distillation gave 2.1 g. original I, along with a fraction, b. below 85°; acidification of the latter with HCl and redistillation gave a distillate in which AcEt was detected, while the distillation residue contained Et2NH.HCl. Thus ketones of this type are hydrogenolyzed readily. Heating 14 g. I and 7.5 g. NH2OH.HCl in 40 ml. MeOH 5 hrs., then adding 70 g. CdCl2 in 50 ml. H2O gave a crop of crystals, which were separated, moistened with a little H2O, and subjected to dry distillation, yielding 59% 5-methylisoxazole, b750 121-2°, d20 1.0224, nD20 1.4368; this treated with EtONa in EtOH, then with Et2O, gave a precipitate of Na salt of AcCH2CN, corresponding to 92% yield; this readily gave MeC(:NNPh)CH2CN, m. 100-1°. Heating 13 g. PrCOCH:CHNMe2 with 7.5 g. NH2OH.HCl in MeOH as above 5 hrs., adding 3 volumes H2O, and extracting with Et2O gave 89% 5-propylisoxazole, b. 161-1.5°, d20 0.9682, nD20 1.4460; with EtONa-EtOH this gave 91.4% Na salt or PrCOCH2CN; phenylhydrazone of the ketone, m. 96°. AcCH:CHNMe2 (5 g.) and 4.5 g. NCCH2CONH2 in 50 ml. H2O refluxed 2 hrs., the mixture cooled, filtered, and the filtrate heated 2 hrs. longer gave 65% (total) 2-hydroxy-3-cyano-6-methylpyridine, m. 278-80°; a 59% yield is obtained when the amino ketone is prepared in situ by treating AcCH:CHCl with aqueous Me2NH and then following the above procedure. Similarly PrCOCH:CHNMe2 and NCCH2CONH2 gave in 5 hrs. 72% 2-hydroxy-3-cyano-6-propylpyridine, m. 147-8°, while iso-BuCOCH:CHNMe2 gave 74.8 % 6-iso-Bu homolog, m. 148-9° (from EtOH). To MeMgI from 47 g. MeI in 250 ml. Et2O was added with good cooling 41 g. AcCH:CHNMe2, yielding an oil which soon solidified; the mixture was treated after 3 hrs. with 10% HCl and extracted with Et2O yielding 19.8% AcCH:CHMe, b. 121-3°, d20 0.8573, nD20 1.4390; 2,4-dinitrophenylhydrazone, m. 153-4°. Refluxing 25 g. AcCH:CHNMe2 and 52 g. MeI 6 hrs., cooling, adding 50 ml. H2O, heating 0.5 hr., steam distilling the MeI, extracting with Et2O, and distilling the extract gave 17.5% AcCMe:CHOH, b. 145-8°, m. 72°. AcCH:CHNMe2 (6 g.) and 9 g. MeI in C6H6 refluxed 4 hrs. and the mixture allowed to stand several days gave 33% of a crystalline addition product, C7H14ONI, decompose 120-2°, yielding with hot H2O AcCMe:CHOH, identical with the above specimen. In the experiment, the researchers used many compounds, for example, 5-Methylisoxazole (cas: 5765-44-6Safety of 5-Methylisoxazole).
5-Methylisoxazole (cas: 5765-44-6) 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. Isoxazole can be synthesised via a variety of methods. Examples include via a 1,3-dipolar cycloaddition of nitrile oxides with alkynes.Safety of 5-Methylisoxazole
Referemce:
Isoxazole – Wikipedia,
Isoxazole | C3H3NO – PubChem