Khomutov, R. M. published the artcileHydroxylamine derivatives. IX. Synthesis of some O-substituted hydroxylamines, Computed Properties of 6084-58-8, the publication is Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya (1967), 1820-3, database is CAplus.
Saturation of 150 g. dry MeCN in 170 ml. EtOH with HCl at 0-5¡ã and keeping 2 days in the cold gave a precipitate of Et acetimidoacetate-HCl, which was separated and treated with aqueous NaOH at -10¡ã, then with 275 g. NH2OH.HCl in C6H6-H2O and stirred 1 hr. at room temperature to yield 45-50% MeC(:NOH)OEt (I), m. 32¡ã, b12 62¡ã. I was converted to the Na salt by MeONa in MeOH and treated with an alkyl halide to give the following MeC(:NOR)OEt (II): (R, % yield, b.p., and n20D given): Et, 70, b55 60¡ã, 1.4141; iso-Pr 84, 134-6¡ã, 1.4155; iso-Bu, 81, 160¡ã, 1.4240; MeSCH2CH2, 34, b7 85-7¡ã, -; PhCH2, 75, b12 122¡ã, 1.5030. II in Et2O was treated with 1 mole H2O and HCl in Et2O to yield on standing the following RONH2.Hcl (R and m.p. given): Et, 128¡ã; iso-Pr, 85-6.5¡ã; iso-Bu 129.5-30.5¡ã; MeSCH2CH2, 96¡ã (decomposition); PhCH2, 224-6¡ã (free base b3 64-4.5¡ã). BrCH2CO2K (0.32 mole) in H2O treated with 0.32 mole KOH and 0.32 mole I 0.5 hr. at 35¡ã, then diluted at -10¡ã with (CH2Cl)2 and acidifying with HCl, then evaporating in vacuo, gave a residue that on reevapn. with HCl gave 65-70% aminoxyacetic acid-HCl, m. 150-1¡ã (iso-PrOH); heating with EtOH-HCl gave the Et ester HCl salt, m. 115-16¡ã, while heating with benzyl alc. in the presence of p-MeC6H4SO3H in C6H6 gave, after azeotropic removal of H2O, 77% benzyl aminoxyacetate, m. 135-7¡ã. Heating Me N-(ethylidenethoxy)aminoxypropionate in concentrated HCl 2.5 hrs. gave on evaporation 80% free acid-HCl, m. 151¡ã, which with benzyl alc. as above gave the benzyl ester of ¦Â-aminoxypropionic acid, m. 112-14¡ã. I and CF2:CFCl kept in an autoclave with alc. EtONa several days gave 85% MeC(OEt):NOCF2CHFCl, b12 61-2.5¡ã. CCl3CH2OH and ClNH2 in the presence of EtONa in Et2O at -10¡ã, then at room temperature 1 day, gave CCl3CH2ONH2.HCl, m. 196-7¡ã (iso-PrOH), after saturation of the crude product with dry HCl in Et2O.
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya published new progress about 6084-58-8. 6084-58-8 belongs to catalysis-chemistry, auxiliary class Salt,Amine,Aliphatic hydrocarbon chain, name is O-Isobutylhydroxylamine hydrochloride, and the molecular formula is C4H12ClNO, Computed Properties of 6084-58-8.
Referemce:
https://courses.lumenlearning.com/boundless-chemistry/chapter/catalysis/,
Catalysis – Wikipedia