Method used for preparing substituted 1, 3-malononitrile
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A technology of malononitrile and conversion conditions, which is applied in the preparation of carboxylic acid nitrile, chemical instruments and methods, and the preparation of organic compounds, etc., can solve the problems of long reaction time and low yield, and achieve easy operation and good substrate compatibility Sexual, wide-ranging effects
Inactive Publication Date: 2019-07-26
FUDAN UNIV
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[0002] The prior art discloses that the Knoevenagel condensation between carbonyl compounds and active methylene compounds is an important reaction to form carbon-carbon double bonds, and the methylene compounds generated by the reaction have a wide range of applications in industry, agriculture, medicine and biological sciences. It is also an important intermediate in organic synthesis reactions; this type of reaction is usually catalyzed by alkali or Lewis acid, and is carried out in liquid phase, especially in organic solvent, by heating, and the generally required reaction time is longer, and The yield is not high
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Embodiment 1
[0019] Using 4-methoxybenzaldehyde as raw material, it is prepared according to the general method, and the yield is 98%. The NMR spectrum data of the product are as follows: 1 H NMR (CDCl 3 ,500MHz)δ7.91(d,J=8.1Hz,2H),7.65(s,1H),7.01(d,J=8.1Hz,2H),3.92(s,3H); 13 C NMR (CDCl 3 , 125MHz) δ164.98, 158.97, 133.59, 124.19, 115.29, 114.55, 113.47, 78.81, 55.94.
Embodiment 2
[0021] Using 3-methoxy-4-hydroxybenzaldehyde as raw material, it is prepared according to the general method, and the yield is 99%. The NMR spectrum data of the product are as follows: 1 H NMR (CDCl 3 ,500MHz)δ7.72(s,1H),7.63(s,1H),7.31(d,J=8.1Hz,1H),7.01(d,J=8.1Hz,1H),6.39(s,1H), 3.98(s,1H); 13 C NMR (CDCl 3 , 125MHz) δ159.36, 152.28, 147.20, 129.08, 124.13, 115.37, 114.51, 113.74, 110.63, 78.34, 56.36.
Embodiment 3
[0023] Using 3,4-dimethoxybenzaldehyde as raw material, it is prepared according to the general method, and the yield is 97%. The NMR spectrum data of the product are as follows: 1 H NMR (CDCl 3 ,500MHz)δ7.67(s,1H),7.64(s,1H),7.38(d,J=7.9Hz,1H),6.95(d,J=7.9Hz,1H),3.98(s,3H), 3.94(s,3H); 13 C NMR (CDCl 3 , 125MHz) δ159.17, 155.00, 149.67, 128.20, 124.38, 114.47, 113.64, 111.24, 111.01, 78.54, 56.38, 56.16.
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Abstract
The invention belongs to the field of fine chemical product preparation and medicine intermediate synthesis, and relates to a method used for preparing substituted 1, 3-malononitrile. According to themethod, an aldehyde or a ketone and malononitrile are subjected to condensation reaction to prepare substituted 1, 3-malononitrile, wherein water is taken as a solvent, the aldehyde or the ketone andmalononitrile are subjected to Knoevenagel condensation under catalytic effect of zinc proline so as to obtain the corresponding substituted 1, 3-malononitrile. The method conditions are mild; operation is convenient; water is taken as a reaction solvent, so that the method is friendly to the environment; and the application prospect is promising.
Description
technical field [0001] The invention belongs to the technical field of preparation of fine chemical products and synthesis of pharmaceutical intermediates, and relates to a method for preparing substituted 1,3-propanedinitrile, in particular to the preparation of substituted 1,3-propanedinitrile by condensation of aldehyde or ketone with malononitrile The dinitrile method. Background technique [0002] The prior art discloses that the Knoevenagel condensation between carbonyl compounds and active methylene compounds is an important reaction to form carbon-carbon double bonds, and the methylene compounds generated by the reaction have a wide range of applications in industry, agriculture, medicine and biological sciences. It is also an important intermediate in organic synthesis reactions; this type of reaction is usually catalyzed by alkali or Lewis acid, and is carried out in liquid phase, especially in organic solvent, by heating, and the generally required reaction time i...
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