[C:1]([CH2:3][CH2:4][NH:5][CH2:6][CH2:7][C:8]#[N:9])#[N:2].S([O-])([O-])(=O)=[O:11].[Mg+2].OO.[C:18]([OH:23])(=[O:22])[C:19]([OH:21])=[O:20]>CC(C)=O.C[Re](=O)(=O)=O.C(OCC)(=O)C>[C:18]([OH:23])(=[O:22])[C:19]([OH:21])=[O:20].[C:1]([CH2:3][CH2:4][N:5]([CH2:6][CH2:7][C:8]#[N:9])[OH:11])#[N:2]Bis(2-cyanoethyl)amine (3.0 g, 0.0224 mole) was added with ethyl acetate (15 ml) and anhydrous magnesium sulfate (3 g), and the mixture was stirred at room temperature. A solution of methyltrioxorhenium (0.0183 g, 0.0734 mmole) dissolved in 35% aqueous hydrogen peroxide (2.9 g, 0.029 mole) was added dropwise to the mixture while internal temperature was kept at from 20° C. to 30° C. After the reaction mixture was stirred at room temperature for 1 hour, the magnesium sulfate was removed by filtration, and the filtrate was added with a solution of oxalic acid (2.2 g, 0.224 mole) dissolved in acetone (8 ml). The mixture was stirred for 30 minutes under ice cooling, and the precipitated crystals were collected by filtration to obtain oxalic acid salt of N,N-bis(2-cyanoethyl)hydroxylamine (4.2 g, yield: 75.0%) having melting point of 129-130° C. Chemical structure of the product was analyzed by 1H-NMR, mass spectrometry and elemental analysis. 1H-NMR (DMSO-D6) σ (ppm) (multiplicity, integrated value): 12.0-9.50 (br, 2H), 2.77 (t, 4H), 2.58 (t, 4H). Elemental analysis, calculated for C8H11N3O5 : C, 41.92; H, 4.84; N, 18.33, found: C, 42.50; H, 4.74; N, 18.38.
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