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Synthetic routes of 4-Chloro-7-hydroxy-6-methoxy-quinoline-3-carbonitrile: An Overview in Chemical Industry
4-Chloro-7-hydroxy-6-methoxy-quinoline-3-carbonitrile (CHMQ) is an organic compound that is used in various applications in the chemical industry.
It is a colorless liquid with a distinctive odor and is highly soluble in water.
It is a versatile compound that can be synthesized through several routes, each with its unique advantages and disadvantages.
This article provides an overview of the synthetic routes of CHMQ in the chemical industry.
Route 1: Hydrolysis of 4-Chloro-3-nitro-7-hydroxy-6-methoxy-quinoline-2-carbonitrile
This is the most common route for the synthesis of CHMQ.
It involves the hydrolysis of 4-chloro-3-nitro-7-hydroxy-6-methoxy-quinoline-2-carbonitrile in the presence of a strong acid catalyst, such as hydrochloric acid.
The reaction proceeds in several steps, including the formation of an intermediate nitrile, followed by the removal of the nitro group by hydrolysis.
The resulting intermediate is then reduced to form the final product, CHMQ.
Advantages of this route include the high yield of product, ease of operation, and low cost.
However, the use of strong acids requires caution and careful handling, and the resulting product may require further purification to remove any impurities.
Route 2: Reduction of 4-Chloro-7-nitro-6-hydroxy-5-methoxy-2H-chromen-2-one
Another route for the synthesis of CHMQ involves the reduction of 4-chloro-7-nitro-6-hydroxy-5-methoxy-2H-chromen-2-one, a compound that is readily available in the market.
The reduction is typically carried out using a reducing agent, such as lithium aluminum hydride (LAH), in the presence of an organic solvent, such as N,N-dimethylformamide (DMF).
The reaction proceeds via a series of steps, including the formation of an intermediate nitroso compound, followed by the reduction of the nitro group to form the final product, CHMQ.
The advantage of this route is that it provides a more convenient and safer method for the synthesis of CHMQ compared to the use of strong acids.
However, the reduction using LAH requires careful handling, as it is highly reactive and can cause fires or explosions if not handled correctly.
Moreover, the resulting product may still require further purification to remove any impurities.
Route 3: Direct Nitration and Hydrolysis of Quinoline-3-carboxylic acid
This is another route for the synthesis of CHMQ that involves the direct nitration and hydrolysis of quinoline-3-carboxylic acid.
The nitration is typically carried out using a nitrating agent, such as nitric acid, in the presence of a solvent, such as acetone.
The resulting nitro compound is then hydrolyzed using a strong acid, such as hydrochloric acid, to form the final product, CHMQ.
The advantage of this route is that it provides a straightforward and efficient method for the synthesis of CHMQ.
However, the use of strong acids and nitrating agents requires careful handling and may require additional purification steps to remove any impurities.
Overall, the synthetic routes of 4-Chloro-7-hydroxy-6-methoxy-quinoline-3-carbon