反应 #52102

反应方程式

5-bromo-2-chloro-N-(2-hydroxyamino-ethyl)-benzamide

acetic anhydride

formic acid

→

title compound

收率 55.0%

5-Bromo-2-chloro-N-[2-(N-formyl-N-hydroxy-amino)-ethyl]-benzamide

收率 55.0%

溶剂

pyridine

反应条件

后处理

1. 1
   其他the pyridine removed in vacuo
2. 2
   洗涤The resulting solid was washed with ether/acetonitrile (9:1)

实验过程

A mixture of acetic anhydride (2 mL) and formic acid (1 mL) was allowed to stand at 55° C. for 2.5 h. After cooling to 0° C., the resulting mixed anhydride (0.5 mL) was added to a solution of 5-bromo-2-chloro-N-(2-hydroxyamino-ethyl)-benzamide (0.7 g, 2.4 mmol) in pyridine (6 mL) at 0° C. under an argon atmosphere. The reaction mixture was stirred for 1 h and the pyridine removed in vacuo. The residue was chased twice with water and twice with MeOH. The resulting solid was washed with ether/acetonitrile (9:1) to provide the title compound (0.42 g, 55%) as a white solid. 1H NMR* (400 MHz, CD3OD): δ 8.35 (s, 0.5H); 7.95 (s, 0.5H); 7.58 (m, 2H); 7.38 (m, 1H); 3.78 (m, 1H); 3.73 (m, 1H); 3.62 (m, 2H). * 1:1 mixture of rotamers. ESMS: M+H=321.

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