CN110003203B - Method for synthesizing 2-acetyl-1, 10-phenanthroline - Google Patents
Method for synthesizing 2-acetyl-1, 10-phenanthroline Download PDFInfo
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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Abstract
The invention discloses a method for synthesizing 2-acetyl-1, 10-phenanthroline, which comprises the steps of taking 1, 10-phenanthroline as a raw material, synthesizing 2-cyano-1, 10-phenanthroline with trimethylsilyl cyanide, trifluoromethanesulfonic anhydride and 1, 8-diazabicycloundecane-7-ene, and reacting 2-cyano-1, 10-phenanthroline with methyllithium to obtain 2-acetyl-1, 10-phenanthroline. The method adopts a two-step synthesis method to prepare the 2-acetyl-1, 10-phenanthroline, is beneficial to the improvement of yield, and is purified by quenching with saturated sodium bicarbonate solution, extracting with dichloromethane and washing with saturated sodium chloride solution after the first step is finished, so that the influence of impurities generated in the first step on the second step is controlled to the minimum.
Description
Technical Field
The invention belongs to the field of chemical industry, and particularly relates to a method for synthesizing 2-acetyl-1, 10-phenanthroline.
Background
The synthesis of 2-acetyl-1, 10-phenanthroline generally comprises the steps of reacting 8-aminoquinoline with amyl-2-enal under the action of concentrated hydrochloric acid to obtain 2-ethyl-1, 10-phenanthroline, and oxidizing to obtain 2-acetyl-1, 10-phenanthroline, wherein a large amount of hydrochloric acid is consumed in the reaction process, great requirements are made on reaction equipment, meanwhile, a large amount of waste acid needs to be treated, and the yield is generally low.
In addition, the target product can be obtained by a side chain alkylation method by using 1, 10-phenanthroline as an initiator, and the yield of the desired unilaterally substituted alkylated phenanthroline product is low, the product is complex and difficult to separate due to low reaction selectivity.
Disclosure of Invention
The purpose of the invention is as follows: the invention aims to provide a synthetic method of 2-acetyl-1, 10-phenanthroline aiming at the defects of the prior art.
The technical scheme is as follows: in order to achieve the above object, the present invention is specifically realized as follows: a method for synthesizing 2-acetyl-1, 10-phenanthroline is characterized by adopting 1, 10-phenanthroline as a raw material to synthesize 2-cyano-1, 10-phenanthroline with trimethylsilyl cyanide, trifluoromethanesulfonic anhydride and 1, 8-diazabicycloundeca-7-ene, and then reacting the 2-cyano-1, 10-phenanthroline with methyllithium to obtain the 2-acetyl-1, 10-phenanthroline.
Specifically, the method comprises the following steps:
(1) adding 1, 10-phenanthroline and dichloroethane into a container according to a mass ratio of 1: 50-100, then placing the container under an ice water bath for stirring, adding trifluoromethanesulfonic anhydride, wherein the mass ratio of the added amount of trifluoromethanesulfonic anhydride to 1, 10-phenanthroline is 1: 1-4, then placing the container under room temperature for stirring for 1 hour, adding trimethylcyanosilane, the mass ratio of the added amount of trimethylcyanosilane to 1, 10-phenanthroline is 2-5: 1, then heating the container to 84 ℃, continuing stirring for 4 hours, finally adding 1, 8-diazabicycloundecene-7-ene, the mass ratio of the added amount of 1, 8-diazabicycloundecene-7-ene to 1, 10-phenanthroline is 0.5-3: 1, stirring for 17 hours at 84 ℃, cooling the mixed solution to room temperature, sequentially quenching with a saturated sodium bicarbonate solution, extracting with dichloromethane, washing with a saturated sodium chloride solution, performing dichloromethane extraction to form an organic phase and a water phase for layering, adding hydrochloric acid into the organic phase solution to adjust the pH to 5-6, separating the organic phase from the water phase, collecting and treating the water phase, drying the organic phase with anhydrous sodium sulfate, adding activated carbon for decoloring, filtering, performing reduced pressure concentration, and recrystallizing with anhydrous ethanol with the mass of 2-4 times of that of 1, 10-phenanthroline to obtain 2-cyano-1, 10-phenanthroline;
(2) adding 2-cyano-1, 10-phenanthroline into a reactor, adding a toluene solution which is 10-50 times of the mass of 2-cyano-1, 10-phenanthroline, stirring at-78 ℃, adding a methyllithium solution which is 1-5 times of the mass of 2-cyano-1, 10-phenanthroline, placing the reactor at room temperature, stirring for 12 hours, transferring the reactor into an ice water bath after stirring, adding water quenching reaction, acidifying with hydrochloric acid, adjusting the pH of the separated water phase to 9-10 with sodium hydroxide, extracting with dichloromethane, separating an organic phase, and drying the organic phase with anhydrous sodium sulfate to obtain 2-acetyl-1, 10-phenanthroline.
Wherein, in the step (1), nitrogen is filled into the container when the 1, 10-phenanthroline and dichloroethane are added into the container.
Wherein, the container in the step (1) is baked at 105 ℃.
Wherein, the condition of-78 ℃ in the step (2) adopts an ethyl acetate bath in a liquid nitrogen environment.
Wherein the using amount of the dichloromethane in the extraction of the dichloromethane in the step (1) is 2-4 times of the mass of 1, 10-phenanthroline.
Wherein the using amount of the saturated sodium chloride solution in the step (1) is 2-4 times of the mass of 1, 10-phenanthroline during washing.
The method comprises the following steps of (1) quenching by using a saturated sodium bicarbonate solution, extracting by using dichloromethane, and washing by using a saturated sodium chloride solution, wherein the main purposes of the quenching by using the saturated sodium bicarbonate solution, the washing by using the saturated sodium chloride solution are to consume unreacted trifluoromethanesulfonic anhydride (no trifluoromethanesulfonic anhydride exists in thin-layer chromatography TLC detection), the dichloromethane extraction is to extract an organic product in the dichloromethane (three times of dichloromethane with the mass of 3-5 times that of 1, 10-phenanthroline), and the washing by using the saturated sodium chloride solution is to wash off an inorganic substance in the dichloromethane (three times of washing by using the saturated sodium chloride solution with the mass of 3-5 times that of 1, 10-.
The reaction structural formula of the invention is as follows:
has the advantages that: compared with the prior art, the invention has the following advantages:
(1) the method adopts a two-step synthesis method to prepare the 2-acetyl-1, 10-phenanthroline, so that the yield is improved, and after the first step is finished, the 2-acetyl-1, 10-phenanthroline is purified by quenching with a saturated sodium bicarbonate solution, extracting with dichloromethane and washing with a saturated sodium chloride solution, so that the influence of impurities generated in the first step on the second step is controlled to be minimum;
(2) the raw materials adopted by the method are wide in source and easy to obtain, the cost of the raw materials is low, the method has considerable economic benefit, and especially when the raw materials are produced and prepared in a large scale, the cost of the traditional method can be saved by 15-20%;
(3) the invention strictly controls the reaction temperature in the first step of reaction, and controls the temperature to be the boiling point of dichloroethane, so the temperature is exactly the reflux temperature;
(4) the method has high yield, and in the first step, the nitrogen atom is activated by using trifluoromethanesulfonic anhydride, so that a nitrogen-containing heterocycle of phenanthroline is activated, the reaction activity is increased, and the reaction selectivity is improved;
(5) the method has the advantages of simple treatment after reaction, simple operation and low energy consumption, adopts ethanol recrystallization for purification, and can improve the purification efficiency.
Detailed Description
Example 1:
a method for preparing 2-acetyl-1, 10-phenanthroline comprises the steps of adding 1, 10-phenanthroline and dichloroethane according to a mass ratio of 1:50 into a container, then placing the container under an ice water bath for stirring, adding trifluoromethanesulfonic anhydride, wherein the mass ratio of the added amount of trifluoromethanesulfonic anhydride to 1, 10-phenanthroline is 1:1, then placing the container at room temperature for stirring for 1 hour, adding trimethylsilyl cyanide, the mass ratio of the added amount of trimethylsilyl cyanide to 1, 10-phenanthroline is 4:1, then heating the container to 84 ℃, continuing stirring for 4 hours, finally adding 1, 8-diazabicycloundecene-7-ene (DBU), wherein the mass ratio of the added amount of 1, 8-diazabicycloundecene-7-ene (DBU) to 1, 10-phenanthroline is 0.5:1, stirring for 17 hours at 84 ℃, cooling the mixed solution to room temperature, sequentially quenching with a saturated sodium bicarbonate solution, extracting with dichloromethane, washing with a saturated sodium chloride solution, performing dichloromethane extraction to form an organic phase and a water phase for layering, adding hydrochloric acid into the organic phase solution to adjust the pH value to 5-6, separating the organic phase from the water phase, collecting and treating the water phase, drying the organic phase with anhydrous sodium sulfate, adding activated carbon for decoloring, filtering, performing reduced pressure concentration, and recrystallizing with anhydrous ethanol with 2 times of the mass of 1, 10-phenanthroline to obtain 2-cyano-1, 10-phenanthroline; adding 2-cyano-1, 10-phenanthroline into a reactor, adding a toluene solution with the mass of 10 times that of 2-cyano-1, 10-phenanthroline, stirring at-78 ℃, adding a methyllithium solution with the same mass of 2-cyano-1, 10-phenanthroline, placing the reactor at room temperature, stirring for 12 hours, transferring the reactor into an ice water bath after stirring, adding water for quenching reaction, acidifying with hydrochloric acid, adjusting the pH of the separated water phase to 9-10 with sodium hydroxide, extracting with dichloromethane to separate an organic phase, drying the organic phase with anhydrous sodium sulfate to obtain 2-acetyl-1, 10-phenanthroline, wherein the container is filled with nitrogen when the 1, 10-phenanthroline and dichloroethane in the step (1) are added into the container, baking the container in the step (1) at 105 ℃, adopting an EA (ethylene-acetic acid) bath at-78 ℃ in the step (2) in a liquid nitrogen environment, wherein the using amount of dichloromethane in the step (1) during extraction of dichloromethane is 2-4 times of the mass of 1, 10-phenanthroline, and the using amount of a saturated sodium chloride solution in the step (1) during washing of the saturated sodium chloride solution is 2-4 times of the mass of 1, 10-phenanthroline.
Example 2:
referring to example 1, a method for preparing 2-acetyl-1, 10-phenanthroline, comprising adding to a vessel at a mass ratio of 1: adding 1, 10-phenanthroline and dichloroethane to 100, placing the container in an ice water bath for stirring, adding trifluoromethanesulfonic anhydride, wherein the mass ratio of the added trifluoromethanesulfonic anhydride to 1, 10-phenanthroline is 1: 4, then placing the container at room temperature for stirring for 1 hour, adding trimethylcyanogen silane, wherein the mass ratio of the added trimethylcyanogen silane to 1, 10-phenanthroline is 2:1, then heating the container to 84 ℃, continuing to stir for 4 hours, finally adding 1, 8-diazabicycloundecane-7-ene (DBU), the mass ratio of the added 1, 8-diazabicycloundecane-7-ene (DBU) to 1, 10-phenanthroline is 3:1, stirring for 17 hours at 84 ℃, cooling to room temperature, and sequentially quenching with a saturated sodium bicarbonate solution, Extracting with dichloromethane, washing with a saturated sodium chloride solution, forming an organic phase and a water phase for layering after extraction with dichloromethane, adding hydrochloric acid into the organic phase solution to adjust the pH to 5-6, separating the organic phase from the water phase, collecting and treating the water phase, drying the organic phase with anhydrous sodium sulfate, adding activated carbon for decolorization, filtering, concentrating under reduced pressure, and recrystallizing with anhydrous ethanol with the mass of 4 times of that of 1, 10-phenanthroline to obtain 2-cyano-1, 10-phenanthroline; adding 2-cyano-1, 10-phenanthroline into a reactor, adding a toluene solution 50 times of the mass of 2-cyano-1, 10-phenanthroline, stirring at-78 ℃, adding a methyllithium solution 5 times of the mass of 2-cyano-1, 10-phenanthroline, placing the reactor at room temperature, stirring for 12 hours, transferring the reactor into an ice water bath after stirring, adding water quenching reaction, acidifying with hydrochloric acid, adjusting the pH of the separated water phase to 9-10 with sodium hydroxide, extracting with dichloromethane, separating an organic phase, and drying the organic phase with anhydrous sodium sulfate to obtain 2-acetyl-1, 10-phenanthroline.
Example 3:
referring to example 1, a method for preparing 2-acetyl-1, 10-phenanthroline, comprising adding 1, 10-phenanthroline and dichloroethane in a mass ratio of 1:75 to a container, then placing the container in an ice-water bath to stir, adding trifluoromethanesulfonic anhydride in a mass ratio of 1:2 to 1, 10-phenanthroline, then placing the container at room temperature to stir for 1 hour, adding trimethylsilyl cyanide in a mass ratio of 5:1 to 1, 10-phenanthroline, then heating the container to 84 ℃, continuing to stir for 4 hours, finally adding 1, 8-diazabicycloundecen-7-ene (DBU), 1, 8-diazabicycloundecen-7-ene (DBU) in a mass ratio of 1, 10-phenanthroline to 1, 10-phenanthroline is 2:1, stirring for 17 hours at 84 ℃, cooling the mixed solution to room temperature, sequentially quenching with a saturated sodium bicarbonate solution, extracting with dichloromethane, washing with a saturated sodium chloride solution, performing dichloromethane extraction to form an organic phase and a water phase for layering, adding hydrochloric acid into the organic phase solution to adjust the pH value to 5-6, separating the organic phase from the water phase, collecting and treating the water phase, drying the organic phase with anhydrous sodium sulfate, adding activated carbon for decoloring, filtering, performing reduced pressure concentration, and recrystallizing with anhydrous ethanol of which the mass is 3 times that of 1, 10-phenanthroline to obtain 2-cyano-1, 10-phenanthroline; adding 2-cyano-1, 10-phenanthroline into a reactor, adding a toluene solution 20 times of the mass of 2-cyano-1, 10-phenanthroline, stirring at-78 ℃, adding a methyllithium solution 2 times of the mass of 2-cyano-1, 10-phenanthroline, placing the reactor at room temperature, stirring for 12 hours, transferring the reactor into an ice water bath after stirring, adding water quenching reaction, acidifying with hydrochloric acid, adjusting the pH of the separated water phase to 9-10 with sodium hydroxide, extracting with dichloromethane, separating an organic phase, and drying the organic phase with anhydrous sodium sulfate to obtain 2-acetyl-1, 10-phenanthroline.
Example 4:
referring to example 1, a method for preparing 2-acetyl-1, 10-phenanthroline comprises adding 1, 10-phenanthroline and dichloroethane in a mass ratio of 1:60 into a container, then placing the container in an ice water bath for stirring, adding trifluoromethanesulfonic anhydride in a mass ratio of 1:3 to 1, 10-phenanthroline, then placing the container at room temperature for stirring for 1 hour, adding trimethylsilyl cyanide in a mass ratio of 1:1 to 1, 10-phenanthroline, then heating the container to 84 ℃, continuing stirring for 4 hours, finally adding 1, 8-diazabicycloundecene-7-ene in a mass ratio of 0.5-3: 1 to 1, 8-diazabicycloundecene-7-ene, stirring for 17 hours at 84 ℃, cooling the mixed solution to room temperature, sequentially quenching with a saturated sodium bicarbonate solution, extracting with dichloromethane, washing with a saturated sodium chloride solution, performing dichloromethane extraction to form an organic phase and a water phase for layering, adding hydrochloric acid into the organic phase solution to adjust the pH value to 5-6, separating the organic phase from the water phase, collecting and treating the water phase, drying the organic phase with anhydrous sodium sulfate, adding activated carbon for decoloring, filtering, performing reduced pressure concentration, and recrystallizing with anhydrous ethanol of which the mass is 3 times that of 1, 10-phenanthroline to obtain 2-cyano-1, 10-phenanthroline; adding 2-cyano-1, 10-phenanthroline into a reactor, adding a toluene solution 30 times of the mass of 2-cyano-1, 10-phenanthroline, stirring at-78 ℃, adding a methyllithium solution 3 times of the mass of 2-cyano-1, 10-phenanthroline, placing the reactor at room temperature, stirring for 12 hours, transferring the reactor into an ice water bath after stirring, adding water quenching reaction, acidifying with hydrochloric acid, adjusting the pH of the separated water phase to 9-10 with sodium hydroxide, extracting with dichloromethane, separating an organic phase, and drying the organic phase with anhydrous sodium sulfate to obtain 2-acetyl-1, 10-phenanthroline.
Example 5:
referring to example 1, a method for preparing 2-acetyl-1, 10-phenanthroline, comprising adding 1, 10-phenanthroline and dichloroethane to a container in a mass ratio of 1:90, then placing the container in an ice water bath to stir, adding trifluoromethanesulfonic anhydride in a mass ratio of 1:2 to 1, 10-phenanthroline, then placing the container at room temperature to stir for 1 hour, adding trimethylsilyl cyanide in a mass ratio of 4:1, heating the container to 84 ℃, continuously stirring for 4 hours, finally adding 1, 8-diazabicycloundecen-7-ene (DBU), wherein the mass ratio of the added 1, 8-diazabicycloundecen-7-ene (DBU) to 1, 10-phenanthroline is 1.5:1, stirring for 17 hours at 84 ℃, cooling the mixed solution to room temperature, sequentially quenching with saturated sodium bicarbonate solution, extracting with dichloromethane, washing with saturated sodium chloride solution, forming an organic phase and a water phase layer after dichloromethane extraction, adding hydrochloric acid into the organic phase solution to adjust the pH value to 5-6, separating the organic phase from the water phase, collecting and treating the water phase, drying the organic phase with anhydrous sodium sulfate, adding activated carbon for decolorization, filtering, concentrating under reduced pressure, recrystallizing with anhydrous ethanol with the mass of 4 times of 1, 10-phenanthroline to obtain 2-cyano-1, 10-phenanthroline; adding 2-cyano-1, 10-phenanthroline into a reactor, adding a toluene solution 40 times of the mass of 2-cyano-1, 10-phenanthroline, stirring at-78 ℃, adding a methyllithium solution 4 times of the mass of 2-cyano-1, 10-phenanthroline, placing the reactor at room temperature, stirring for 12 hours, transferring the reactor into an ice water bath after stirring, adding water quenching reaction, acidifying with hydrochloric acid, adjusting the pH of the separated water phase to 9-10 with sodium hydroxide, extracting with dichloromethane, separating an organic phase, and drying the organic phase with anhydrous sodium sulfate to obtain 2-acetyl-1, 10-phenanthroline.
Claims (7)
1. A method for synthesizing 2-acetyl-1, 10-phenanthroline is characterized in that 1, 10-phenanthroline is adopted as a raw material to be synthesized into 2-cyano-1, 10-phenanthroline with trimethylsilyl cyanide, trifluoromethanesulfonic anhydride and 1, 8-diazabicycloundecane-7-ene, and then the 2-cyano-1, 10-phenanthroline is reacted with methyllithium to prepare the 2-acetyl-1, 10-phenanthroline.
2. The method for the synthesis of 2-acetyl-1, 10-phenanthroline according to claim 1, characterized in that it comprises the following steps:
(1) adding 1, 10-phenanthroline and dichloroethane into a container according to a mass ratio of 1: 50-100, then placing the container under an ice water bath for stirring, adding trifluoromethanesulfonic anhydride, wherein the mass ratio of the added amount of trifluoromethanesulfonic anhydride to 1, 10-phenanthroline is 1: 1-4, then placing the container under room temperature for stirring for 1 hour, adding trimethylcyanosilane, the mass ratio of the added amount of trimethylcyanosilane to 1, 10-phenanthroline is 2-5: 1, then heating the container to 84 ℃, continuing stirring for 4 hours, finally adding 1, 8-diazabicycloundecene-7-ene, the mass ratio of the added amount of 1, 8-diazabicycloundecene-7-ene to 1, 10-phenanthroline is 0.5-3: 1, stirring for 17 hours at 84 ℃, cooling the mixed solution to room temperature, sequentially quenching with a saturated sodium bicarbonate solution, extracting with dichloromethane, washing with a saturated sodium chloride solution, forming an organic phase and a water phase for layering after extracting with dichloromethane, adding hydrochloric acid into the organic phase solution to adjust the pH to 5-6, collecting and treating the water phase, drying the organic phase with anhydrous sodium sulfate, adding activated carbon for decoloring, filtering, concentrating under reduced pressure, and recrystallizing with anhydrous ethanol 2-4 times the mass of 1, 10-phenanthroline to obtain 2-cyano-1, 10-phenanthroline;
(2) adding 2-cyano-1, 10-phenanthroline into a reactor, adding a toluene solution which is 10-50 times of the mass of 2-cyano-1, 10-phenanthroline, stirring at-78 ℃, adding a methyllithium solution which is 1-5 times of the mass of 2-cyano-1, 10-phenanthroline, placing the reactor at room temperature, stirring for 12 hours, transferring the reactor into an ice water bath after stirring, adding water quenching reaction, acidifying with hydrochloric acid, adjusting the pH of the separated water phase to 9-10 with sodium hydroxide, extracting with dichloromethane, separating an organic phase, and drying the organic phase with anhydrous sodium sulfate to obtain 2-acetyl-1, 10-phenanthroline.
3. The method for synthesizing 2-acetyl-1, 10-phenanthroline according to claim 2, wherein the vessel is subjected to nitrogen charging treatment while the 1, 10-phenanthroline and dichloroethane are added to the vessel in the step (1).
4. The method for the synthesis of 2-acetyl-1, 10-phenanthroline according to claim 2, wherein the vessel in step (1) is baked at 105 ℃.
5. The method for synthesizing 2-acetyl-1, 10-phenanthroline according to claim 2, wherein the-78 ℃ condition in the step (2) is an EA bath in a liquid nitrogen environment.
6. The method for synthesizing 2-acetyl-1, 10-phenanthroline according to claim 2, wherein the amount of dichloromethane used in the extraction with dichloromethane in step (1) is 2-4 times of the mass of 1, 10-phenanthroline.
7. The method for synthesizing 2-acetyl-1, 10-phenanthroline according to claim 2, wherein the amount of the saturated sodium chloride solution used in the step (1) of washing with the saturated sodium chloride solution is 2-4 times of the amount of 1, 10-phenanthroline.
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