[CH2:1]([O:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][C:9]#[N:10])[CH3:2].[NH2:11][OH:12]>CCO>[CH2:1]([O:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][C:9](=[N:11][OH:12])[NH2:10])[CH3:2]A solution of 3-(2-ethoxyethoxy)propanenitrile (1 g, 7 mmol) and NH2OH (50% in water, 0.64 cm3, 10.5 mmol) in EtOH (10 cm3) were heated to reflux for 24 hours, after which the solvent and excess hydroxylamine were removed by rotary evaporator. The residue was freeze-dried and kept in high vacuum line for several hours to give 3(2-ethoxyethoxy)N′-hydroxypropanimidamide (1.2 g, 97.6%) as a colourless oil.
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