Synthetic method of 8-nitroquinoline

A technology of nitroquinoline and o-nitroaniline, applied in the direction of organic chemistry and the like, can solve the problems of high generation of 6-nitroquinoline, unsuitable for industrial production, large environmental pollution, etc., and it is easy to reach the end of the reaction and the end of the reaction. Control, phenomenal effects

Inactive Publication Date: 2019-01-08
HUAIAN WAN BANG SPICE IND CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, the method for preparing 8-nitroquinoline, the first is to adopt quinoline nitration, this method is not suitable for industrial production because the by-product 6-nitroquinoline is generated more, and the yield is low, so it can only be used in the laboratory use
The 2nd, in industrial production, synthetic 8-nitroquinoline is generally o-nitroaniline, glycerol, sulfuric acid cyclization, generates 8-nitroquinoline with arsenic pentoxide as oxidant oxidation, although the method yield is higher High, but arsenic pentoxide is a highly toxic substance, which causes great environmental pollution

Method used

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  • Synthetic method of 8-nitroquinoline

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Add 550 grams of 98% sulfuric acid in a 2L four-necked flask equipped with a condenser, a thermometer, a dropping funnel, a stirrer and a gas absorption device.

[0024] Add 276 grams of o-nitroaniline in batches under a controlled temperature below 80°C, slowly and naturally raise the temperature from room temperature to 70°C-80°C, and continue stirring for 20-30 minutes until completely dissolved.

[0025] Control 70°C-80°C, add 645 grams of glycerin dropwise for about 90 minutes, and keep warm for 60-70 minutes at about 80°C after dropping.

[0026] Add dropwise a solution prepared by dissolving 2.5 grams of iodine and 2.5 grams of potassium iodide in 10 grams of water, and slowly heat up to 130°C after dropping the solution. After about half an hour, purple reflux begins and gas is released, and the gas is absorbed with lye.

[0027] The reaction at 130°C was naturally heated to 140°C for about 1 hour, the color of the reflux gradually changed to colorless, and the ...

Embodiment 2

[0031] In a 2L four-port container equipped with a condenser, a thermometer, a dropping funnel, a stirrer and a gas absorption device

[0032] Add 500 grams of 98% sulfuric acid in the flask.

[0033] Add 276 grams of o-nitroquinoline in batches under control below 90°C, slowly and naturally raise the temperature from room temperature to 80°C-90°C, and continue stirring for 20-30 minutes until completely dissolved.

[0034] Control 80°C-90°C, add 552 grams of glycerol dropwise for about 90 minutes, and keep warm for 30-40 minutes at about 90°C after dropping.

[0035] Add dropwise a solution prepared by dissolving 2 g of iodine and 2 g of potassium iodide in 10 g of water, and slowly raise the temperature to 130°C after dropping, and for about half an hour, purple reflux begins and gas is released, and the gas is absorbed with lye.

[0036] 130 ° C reaction naturally heated to 140 ° C for about 1 hour, the reflux color gradually became clear, and continued to keep warm for 30...

Embodiment 3

[0040] Add 600 grams of 98% sulfuric acid in a 2L four-necked flask equipped with a condenser, a thermometer, a dropping funnel, a stirrer and a gas absorption device.

[0041] Add 276 grams of o-nitroquinoline in batches at a temperature below 70°C, slowly and naturally raise the temperature from room temperature to 60°C-70°C, and continue stirring for 20-30 minutes until completely dissolved.

[0042] Control 60°C-70°C, add 690 grams of glycerin dropwise for about 90 minutes, and keep warm for 75-90 minutes at about 70°C after dropping.

[0043] Add dropwise a solution prepared by dissolving 3 grams of iodine and 3 grams of potassium iodide in water, and slowly raise the temperature to 120°C for about half an hour after dropping, the reaction will naturally heat up and gradually purple reflux and gas will be released, and the gas will be absorbed with lye.

[0044] The reaction at 120°C was naturally heated to 140°C for about 1.5 hours, the color of the reflux gradually beca...

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Abstract

The invention provides a synthetic method of 8-nitroquinoline. The synthetic method comprises the following steps: taking ortho-nitroaniline and glycerinum as raw materials, carrying out dehydration in sulfuric acid, and taking iodine-potassium iodide as an oxidizing agent to cyclize 8-nitroquinoline. At the temperature of 60 to 120 DEG C, glycerinum is added dropwise, the dehydration reaction ofglycerinum and sulfuric acid is mild and controllable, and then the cyclization reaction with ortho-nitroaniline is mild and controllable quickly, so that heat release controllability of sharp reaction cannot be caused. An iodine-potassium iodide water solution is used for taking the place of diarsenic pentoxide as an oxidant, the synthetic method is safe and pollution-free, simple in operation and relatively high in yield. The iodine-potassium iodide catalyst is mild, when a back flow becomes clear from muddy, the reaction is basically finished, the phenomenon is obvious, the reaction endpoint is easy to control, gas phase tracking detection can be realized, the post-treatment is simple, little waste water is generated, and the production process is safe and environmentally-friendly.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and relates to a preparation method of a pharmaceutical intermediate, in particular to a preparation method of 8-nitroquinoline. Background technique [0002] 8-Nitroquinoline is also known as 8-Nitroquinoline, 8-Nitroquinoline, CAS No.: 607-35-2. 8-Nitroquinoline is a pharmaceutical intermediate used in organic synthesis. [0003] At present, the method for preparing 8-nitroquinoline, the first is to adopt quinoline nitration, this method is not suitable for industrial production because the by-product 6-nitroquinoline is generated more, and the yield is low, so it can only be used in the laboratory use. The 2nd, in industrial production, synthetic 8-nitroquinoline is generally o-nitroaniline, glycerol, sulfuric acid cyclization, generates 8-nitroquinoline under oxidation with arsenic pentoxide as oxidant, although the yield of this method is higher High, but arsenic pentoxide is a highly toxi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/18
CPCC07D215/18
Inventor 蒋坤徐少强谢雨
Owner HUAIAN WAN BANG SPICE IND CO LTD
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