Sodium Hydroxide → 2-(2-Ethyl [1,3]dioxolan-2-yl)-N-hydroxy-acetamidine
Reaction equation
[OH-:1].[Na+].Cl.[NH2:4]O.[CH2:6]([C:8]1([CH2:13][C:14]#[N:15])[O:12][CH2:11][CH2:10][O:9]1)[CH3:7]>O.CO>[CH2:6]([C:8]1([CH2:13][C:14]([NH:4][OH:1])=[NH:15])[O:12][CH2:11][CH2:10][O:9]1)[CH3:7]Participants
5
Procedure
A solution of NaOH (1.17 g, 29.3 mmol) in water/methanol (1:1) (18 ml), cooled to 0° C. in an ice bath, is treated with hydroxylamine hydrochloride (1.58 g, 22.78 mmol), with stirring for 5 minutes. (2-Ethyl-[1,3]dioxolan-2-yl)-acetonitrile (1.42 g, 10.125 mmol) is added and the reaction mixture stirred at room temperature for 18 hours, then refluxed for a further 2 hours. The reaction mixture is cooled and partitioned between ethyl acetate and water. The organic phase is dried over MgSO4, filtered, and the solvent evaporated to yield 2-(2-Ethyl [1,3]dioxolan-2-yl)-N-hydroxy-acetamidine. [M+H] 175.21