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ChemicalBook CAS DataBase List Ethyl cyanoglyoxylate-2-oxime
3849-21-6

Ethyl cyanoglyoxylate-2-oxime synthesis

2synthesis methods
Ethyl cyanoacetate

105-56-6

Ethyl cyanoglyoxylate-2-oxime

3849-21-6

Example 1: Preparation of ethyl 2-oxime cyanoacetate To a suspension of ethyl cyanoacetate (1.0 kg, 8.84 mol) and sodium nitrite (0.735 kg, 10.65 mol) in water (0.80 L) was slowly added acetic acid (0.70 kg, 11.66 mol), and the reaction temperature was controlled to be in the range of 0-50°C. The reaction temperature was slowly raised to 23-27 °C over a period of 1 h and the reaction mixture was continuously stirred at this temperature for 1 h. The reaction temperature was then adjusted to the temperature of the reaction mixture. After confirming complete consumption of ethyl cyanoacetate by TLC or GC monitoring, the reaction mixture was extracted with ethyl acetate (5 x 1.5 L). The organic layers were combined and washed sequentially with 10% sodium bicarbonate solution (2 x 1.25 L) and saturated brine (1.25 L). The organic layer was dried over anhydrous sodium sulfate and filtered through a hyflow bed. The solvent was removed by distillation under reduced pressure at 40-45 °C. The resulting solid was stirred with cyclohexane (3.0 L) at 25-30 °C for 30 min, filtered and dried in vacuum at 40-45 °C to give ethyl 2-oxime cyanoacetate 1.14 kg (91.2% yield) with 99.82% HPLC purity.

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Yield:3849-21-6 93%

Reaction Conditions:

with glacial acetic acid;NaNO2 at 0 - 20; for 6.66667 h;

Steps:

General procedure for the synthesis of compound 1

A mixture of ethyl cyanoacetate (11.3 g, 0.1 mol) and 45% acetic acid aqueous solution (45 mL) was stirred at 0 °C for 10 min. Within 90 min, sodium nitrite (21.0 g, 0.3 mol) was added in three times. Then, the reaction system was stirred at room temperature for 5 h. The solvent is removed under pressure and the product was dried to give a yellow solid 1 and used without further purification (Yield 93%).

References:

Guo, Hongmei;Nie, Lifei;Bozorov, Khurshed;Aisa, Haji Akber;Zhao, Jiangyu [Heterocycles,2022,vol. 104,# 6,p. 1085 - 1097] Location in patent:supporting information

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