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Preparation method of 2-acetyl-1, 10-phenanthroline

A technology of phenanthroline and acetyl, which is applied in the field of preparation of 2-acetyl-1,10-phenanthroline, can solve the problems of high storage conditions, unrealized large-scale industrial production, and difficult control.

Active Publication Date: 2021-06-11
TAIZHOU BIOMEDICAL & CHEM IND RES INST CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The above-mentioned preparation method is expensive, the synthesis conditions are too harsh, and the industrialization advantage is not large; at the same time, because trimethylsilyl cyanide is used in the above-mentioned preparation process, the toxicity is relatively high, the synthesis yield is not high, and the operation is complicated
[0003] At the same time, in the prior art, 2-acetyl-1,10-phenanthroline is prepared by using 3-acetylacrolein as a raw material through addition, cyclization, and dehydrogenation, but this raw material 3-acetylpropene There is no industrialized manufacturer of aldehyde (although it can be purchased from commercially available products, but the storage conditions are high, and a large amount of industrial production has not been realized), and the stability of 3-acetylacrolein is not good, and it is easy to polymerize. It is not easy to control the condensation products that lead to the formation of aldehydes and amino groups, resulting in more industrial by-products

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  • Preparation method of 2-acetyl-1, 10-phenanthroline
  • Preparation method of 2-acetyl-1, 10-phenanthroline

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preparation example Construction

[0023] The invention provides a kind of preparation method of 2-acetyl-1,10-phenanthroline, comprising the following steps:

[0024] Mix 8-aminoquinoline, aceguvaldehyde and alcohol organic solvents, and undergo a Schiff base reaction to obtain E-1-(quinoline-8-imino)propane-2-one;

[0025] Mix the E-1-(quinoline-8-imino)propane-2-one with absolute ethanol, add catalyst and pyruvic acid after removing water, and doebner reaction occurs to obtain 2-acetylphenanthroline -4-Formic acid;

[0026] The 2-acetylphenanthroline-4-carboxylic acid undergoes a decarboxylation reaction under alkaline conditions to obtain the 2-acetylphenanthroline-1,10-phenanthroline.

[0027] In the present invention, unless otherwise specified, all raw material components are commercially available products well known to those skilled in the art.

[0028] In the present invention, the preparation process of the 2-acetyl-1,10-phenanthroline is preferably as shown in formula I:

[0029]

[0030] The ...

Embodiment 1

[0057] At room temperature, dissolve 36g (0.25mol) of 8-aminoquinoline in 180mL of ethanol, add dropwise 20g (0.28mol) of methylglyoxal, stir for 3min, react at 55°C for 2h, cool down to -5°C, and keep warm 1h, filter, the obtained filter cake is rinsed with cold ethanol, sucked dry, and vacuum-dried at 55°C for 10h to obtain 50.2g E-1-(quinoline-8-imino)propane-2-one ( Yield 95%, purity 98%);

[0058] After mixing 50g (0.25mol) of E-1-(quinoline-8-imino)propan-2-one and 250mL of anhydrous methanol, reflux for 3h, then add 23g of PPA and 0.5g of vanadic acid, dropwise add 23g (0.26mol) pyruvic acid, heated to reflux for 12h, recovered methanol, added 250mL of purified water and 150mL of dichloromethane, stirred at room temperature for 2h, stood to separate layers, took the organic layer and washed it with water until pH = 7, to obtain 2-acetylphenanthrolephrine Phenyl-4-carboxylic acid;

[0059] The 2-acetylphenanthroline-4-formic acid was adjusted to pH 10.5 with 10% sodium...

Embodiment 2

[0062] At room temperature, dissolve 36g (0.25mol) of 8-aminoquinoline in 180mL of ethanol, dropwise add 20g (0.28mol) of methylglyoxal, stir for 3min, react at 70°C for 2h, cool down to -5°C, and keep warm 1h, filtered, rinsed the obtained filter cake with cold ethanol, sucked dry, and dried in vacuum at 55°C for 10h to obtain 49g of E-1-(quinoline-8-imino)propan-2-one;

[0063] Mix 40g (0.20mol) of E-1-(quinoline-8-imino)propan-2-one and 220mL of anhydrous methanol, reflux for 3h, then add 35g of phosphorus oxychloride, dropwise add 21g (0.24mol ) pyruvic acid, heated to reflux for 15h, reclaimed methanol, added to a mixture of 200mL purified water and 150mL dichloromethane, stirred at room temperature for 2h, stood to separate layers, took the organic layer and washed it with water until pH = 7, to obtain 2-acetyl Phenanthroline-4-carboxylic acid;

[0064] The 2-acetylphenanthroline-4-formic acid is adjusted to pH 10.5 with a mass concentration of 10% sodium hydroxide solu...

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Abstract

The invention relates to the technical field of organic synthesis, in particular to a preparation method of 2-acetyl-1, 10-phenanthroline. The preparation method provided by the invention comprises the following steps: mixing 8-aminoquinoline, pyruvic aldehyde and an alcohol organic solvent, and carrying out Schiff base reaction to obtain E-1-(quinoline-8-imino) propane-2-ketone; mixing the E-1-(quinoline-8-imino) propane-2-ketone and absolute ethyl alcohol, after moisture is removed, adding a catalyst and pyruvic acid, performing a doebner reaction, and obtaining 2-acetyl phenanthroline-4-formic acid; performing a decarboxylation reaction on the 2-acetyl phenanthroline-4-formic acid under the alkaline condition, and obtaining the 2-acetyl-1, 10-phenanthroline. The preparation method has the advantages of simple synthetic route, mild reaction conditions, easy industrial production, and green and friendly preparation raw materials.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a preparation method of 2-acetyl-1,10-phenanthroline. Background technique [0002] At present, 2-acetyl-1,10-phenanthroline is mainly used in photoelectric materials and catalytic materials, which mainly uses 2-bromophenanthroline to extract bromine through butyllithium at -78 °C, and then combine with N , N-dimethylacetamide prepared by reaction. The above-mentioned preparation method is expensive, the synthesis conditions are too harsh, and the industrialization advantage is not large; at the same time, because trimethylsilyl cyanide is used in the above-mentioned preparation process, the toxicity is relatively high, the synthesis yield is not high, and the operation is complicated. [0003] At the same time, in the prior art, 2-acetyl-1,10-phenanthroline is prepared by using 3-acetylacrolein as a raw material through addition, cyclization, and dehydrogenation, but ...

Claims

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Application Information

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IPC IPC(8): C07D471/04
CPCC07D471/04
Inventor 韩得满李运广武承林陈霞
Owner TAIZHOU BIOMEDICAL & CHEM IND RES INST CO LTD
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