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The 4-chloro-3(2H)-pyridazinone, often referred to as 4-CP, is an important intermediate in the production of pharmaceuticals, agrochemicals, and other chemical products.
The chemical structure of 4-CP is shown in Figure 1.
Figure 1: Chemical structure of 4-chloro-3(2H)-pyridazinone
4-CP can be synthesized through several different routes, including the Barger procedure and the Elsholtz method.
However, the most commonly used route involves treating 2-chloropyridine with sodium hydroxide in the presence of a solvent such as ether or benzene.
The reaction can be represented as follows:
2Cl-C5H3N → 4-Cl-C5H3N
The intermediate can then be reduced to form the desired 4-chloro-3(2H)-pyridazinone using a reducing agent such as hydrogen gas in the presence of a catalyst, such as palladium on barium oxide.
The reaction can be represented as follows:
4-Cl-C5H3N + H2 → 4-C5H3NCl
The resulting 4-chloro-3(2H)-pyridazinone can then be purified and isolated using standard methods such as crystallization, distillation, or chromatography.
4-CP has a wide range of applications in the chemical industry due to its versatility and stability.
It can be used as an intermediate for the production of various pharmaceuticals, including anti-inflammatory drugs, anti-bacterial agents, and antidepressants.
4-CP is also used in the production of agrochemicals, such as herbicides, and in the manufacture of other chemical products such as dyes and pigments.
One of the most important uses of 4-CP is in the production of anti-inflammatory drugs such as ibuprofen and naproxen.
These drugs are widely used to relieve pain, reduce inflammation, and lower fever.
The synthesis of ibuprofen from 4-CP is shown in Figure 2.
Figure 2: Synthesis of ibuprofen from 4-CP
In this process, 4-CP is first converted to 2-naphthaleneacetic acid (NAA) through a series of chemical reactions.
The NAA is then condensed with phenol to form ibuprofen.
The use of 4-CP in the production of anti-bacterial agents is another important application in the chemical industry.
4-CP can be converted to the antibiotic gentamicin through a series of chemical reactions, as shown in Figure 3.
Figure 3: Synthesis of gentamicin from 4-CP
The gentamicin is then purified and isolated from the reaction mixture, and can be used to treat a variety of bacterial infections.
In addition to its uses in the pharmaceutical industry, 4-CP is also used in the production of herbicides and other agrochemicals.
One example is the herbicide 2,4-D, which is widely used to control weeds in crops such as corn, soybeans, and wheat.
The synthesis of 2,4-D from 4-CP is shown in Figure 4.
Figure 4: Synthesis of 2,4-D from 4-CP
In this process, 4-CP is first treated with chlorine to form 4-chloro-3,6-dichlorpyridazine, which is then hydrolyzed to form 3,6-dichlorpyridazine.
This intermediate is then fused with a second molecule of 4