Ethylchloro[(4-fluorophenyl)hydrazono]acetate synthesis
- Product Name:Ethylchloro[(4-fluorophenyl)hydrazono]acetate
- CAS Number:37522-19-3
- Molecular formula:C10H10ClFN2O2
- Molecular Weight:244.65
Yield:37522-19-3 81.5%
Reaction Conditions:
Stage #1: 4-fluoroanilinewith hydrogenchloride;sodium nitrite in ethanol;water at 0 - 5; for 0.5 h;
Stage #2: ethyl 2-chloro-3-oxo-butyratewith sodium acetate in ethanol;water at 0 - 25;
Steps:
2 General procedure for preparation intermediates of ethyl 2-chloro-2-(2-arylhydrazono)acetate (21a-21j)
General procedure: Commercially available substituted aniline (63.4mmol) was portionwise added to a solution of concentrated HCl (13mL), ethanol (20mL) and water (7mL). To the above mixture was added dropwise a solution of NaNO2 (4.69g, 69.7mmol) in water (15mL) at 0-5°C. After the completion of addition, the reaction mixture was stirred at this temperature for 30min, and then added into a mixture of ethyl 2-chloroacetoacetate (10.88g, 63.4mmol), anhydrous sodium acetate (15.60g, 190.10mmol), and water (90mL) at 0°C. The reaction mixture was stirred at 0°C for 10min and then at room temperature for 4h. The solid which precipitated was collected by filtration and recrystallized from ethanol to afford light yellow solids (21a-21m) in 75.2-90% yields.
6.3.2
Ethyl 2-chloro-2-(2-(4-fluorophenyl)hydrazono)acetate (21b)
Yellow solid; Yield: 81.5%; M.p.: 109.2-110.4 °C; MS (ESI) m/z(%): 267.0 [M+Na]+.
References:
Liu, Ju;Nie, Minhua;Wang, Yanjing;Hu, Jinxing;Zhang, Feng;Gao, Yanlin;Liu, Yajing;Gong, Ping [European Journal of Medicinal Chemistry,2016,vol. 123,p. 431 - 446]
