Methylhydrazine → O-(2,2-dimethyl-1,3-dioxan-5-yl)Hydroxylamine
Reaction equation
[CH3:1][C:2]1([CH3:20])[O:7][CH2:6][CH:5]([O:8][N:9]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:4][O:3]1.CNN>ClCCl>[CH3:1][C:2]1([CH3:20])[O:7][CH2:6][CH:5]([O:8][NH2:9])[CH2:4][O:3]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirring solution of 2-(2,2-dimethyl-[1,3]dioxan-5-yloxy)-isoindole-1,3-dione (1.72 g, 6.20 mmol) in dichloromethane (15 mL) at 0° C. under nitrogen was added methylhydrazine (0.36 mL, 6.82 mmol) and allowed to warm to room temperature. After stirring for two hours the reaction mixture was concentrated in vacuo and charged with diethylether. The solids were filtered off and the filtrate was collected and concentrated to afford O-(2,2-dimethyl-[1,3]dioxan-5-yl)-hydroxylamine as a yellow oil (0.97 g, 100%). 1H NMR (400 MHz; DMSO-d6) δ 5.98 (bs, 2H), 3.84-3.87 (m, 2H), 3.66-3.68 (m, 2H), 3.30-3.35 (m, 1H), 1.29 (s, 3H), 1.22 (s, 3H); MS (APCI+)=147.9.