2-cyano-N,N-diethyl-3-(4-hydroxy-3-methoxyphenyl)acrylamide synthesis
- Product Name:2-cyano-N,N-diethyl-3-(4-hydroxy-3-methoxyphenyl)acrylamide
- CAS Number:893419-47-1
- Molecular formula:C15H18N2O3
- Molecular Weight:274.32
26391-06-0
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Yield:893419-47-1 92%
Reaction Conditions:
with acetic acid;diethylamine in cyclohexane;Reflux;Solvent;
Steps:
2 Example 2 - Preparation of (E)-N,N-diethyl-2-cyano-3-(3-methoxy-4-hydroxyphenyl) acrylamide (Formula IV)
Cyclohexane (650 mL), vanillin (36 g), N,N-diethyl-cyanoacetamide (35.3 g), glacial acetic acid (2.90 g) and diethylamine (3.9 g) were added to a 1 L flask equipped with a water separator and stirred at room temperature to form a reaction mixture. The reaction mixture was heated under reflux for 6 to 8 hours. The water formed was removed by means of the water separator. After the reaction mixture was cooled, a small amount of (E)-N, N-diethyl-2-cyano-3-(3-methoxy-4- hydroxyphenyl) acrylamide was then added to the reaction mixture. The reaction mixture was then cooled to 25 °C and filtered to obtain a solid. The solid was subsequently washed with toluene and then dried to obtain 58.0 g of (E)-N,N- diethyl-2-cyano-3-(3-methoxy-4-hydroxyphenyl) acrylamide. The yield was 92%. The HPLC purity of the E-isomer was 99.4%.
References:
WO2013/149566,2013,A1 Location in patent:Paragraph 0040
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