3-Chloro-4-cyanopyridine CAS 68325-15-5

3-Chloro-4-cyanopyridine, chemical formula C6H3ClN2, CAS 68325-15-5. It is a pyridine compound containing chlorine and cyano groups. It exists in a solid form from white to light yellow. It has a certain polarity due to its chemical structure containing chlorine and cyanide groups. This polarity attribute may play an important role in its interactions and reactions in solution. In different research fields and industrial applications, 3 Chloro-4-cyanopyridine can also be used to synthesize chemicals such as pesticides, dye additives, coatings, and polymers. However, specific uses and synthesis methods may vary depending on specific compounds, reaction conditions, and target requirements.

3-Chloro-4-cyanopyridine is an organic compound with a wide range of applications.

1. Pharmaceutical field:

3 Chloro-4-cyanopyridine is widely used as an important intermediate in the pharmaceutical field. It can be used to synthesize various drugs, especially anticancer drugs and bioactive molecules. For example, it can be used to synthesize anticancer drugs such as Famitinib, Sitravatinib, and Infigratinib. In addition, 3 Chloro-4-cyanopyridine can also synthesize other drugs, such as tyrosine kinase inhibitors, antiviral drugs, and anti infective agents.

2. Pesticides:

3 Chloro-4-cyanopyridine also has certain applications in the field of pesticides. It can be used as an intermediate in the synthesis of insecticides and herbicides. These compounds can be used to control pests and weeds in crops, and improve the yield and quality of farmland.

3. Chemical synthesis:

3 Chloro-4-cyanopyridine is also an important intermediate for synthesizing other organic compounds. It can be used to synthesize various functional compounds, such as cyano substituted pyridine derivatives, heterocyclic compounds, and potential fluorescent dyes. These compounds have extensive applications in fields such as materials science, chemical biology, and drug research.

4. Research and laboratory use:

3 Chloro-4-cyanopyridine is used as a reagent and chemical standard in research and laboratories. It can be used in material analysis, synthesis reactions, and organic chemistry research. In addition, it can also be used as a detection reagent and impurity reference material.

5. Intermediate synthesis:

3 Chloro-4-cyanopyridine is an important intermediate for the synthesis of various organic compounds. It can produce various compounds with different heterologous substituents through reactions and functionalization modifications. This compound can serve as a precursor for initiators, catalysts, targeted molecules, and bioactive compounds.

6. Drug synthesis:

3 Chloro-4-cyanopyridine has a wide range of applications in the field of drug synthesis. It can be used to synthesize anticancer drugs, antiviral drugs, anti infective agents, hormone drugs, and neurotransmitter drugs. By reacting with other molecular groups, 3 Chloro-4-cyanopyridine can be converted into compounds with specific biological activity.

7. Synthesis of heterocyclic compounds:

3 Chloro-4-cyanopyridine can be used to synthesize compounds with heterocyclic structures. Through further functionalization reactions, it can react with different reagents or ligands to form various heterocyclic compounds, such as structures of zine, thiophene, and pyrazole. These heterocyclic compounds play an important role in drug research and materials science.

8. Synthesis of functional chemicals:
Due to the presence of chlorine and cyano groups in 3-Chloro-4-cyanopyridine, it can be further modified to form more functional compounds. For example, it can introduce different substituents through nucleophilic substitution, free radical reactions, reduction reactions, and imination reactions to generate compounds with specific properties and functions.

Method 1:

In a reactor equipped with a reflux condenser at 20 ℃ and a nitrogen atmosphere, 4-cyanopyridine N-oxide (250g, 2.08mol) was added in batches to the stirred PCl5 (599.94g, 2.88mol) and POCl3 (800mL, 8.71mol) suspensions. During the feeding period, the temperature rises to 41 ℃. Stir the mixture at 100 ℃ for 3 hours, then cool to 95 ℃ and transfer to a mixture of 6MHCl (200mL) and 6:4 ice water mixture (5994g). Control the transfer rate to keep the temperature below 15 ℃ (about 35 minutes). The brown solution formed by cooling is below 5 ℃, and 33% NaOH aqueous solution (about 4.5L) is added to adjust the pH to 4.15, while maintaining the temperature below 5 ℃. Filter the resulting beige precipitate and use water (4 × Wash thoroughly and drain as much as possible. Suspend the residue in water (1.5L) and n-heptane (7L) and stir at 30 ℃ for 1 hour. Separate the aqueous phase and further use n-heptane (2 × 2L) Extraction, stirring at 30 ℃ for 30 minutes each time. The merged heptane layer was dried (Na2SO4136g), filtered, and the resulting solution was concentrated under reduced pressure to a weight of 1.9kg (approximately 3L), at which point the product began to crystallize. Cool the mixture to 0 ℃, stir for 1.5 hours, then filter the 3-Chloro-4-cyanopyridine and use cold n-heptane (2 × Wash with 125mL and dry at room temperature in a circulating air dryer to obtain crystalline solid products (129.08g, 44.8%); m. P.73.4 ℃.

Method 2:

Add 2.5M n-BuLi (7.7mL) to a stirred solution of 2,2,6,6-tetramethylpiperidine (2.85g, 20.2mmol) in THF (40mL) at -30 ℃ and N2. Bring the solution to 0 ℃, stir for 15 minutes, and then cool to -80 ℃. Slowly add isonitrile (1 g, 9.6 mmol) from THF (10 mL) to the mixture within 15 minutes. After stirring at -80 ℃ for 30 minutes, add C2Cl6 (4.73g, 20.2mmol) THF (10mL) solution dropwise within 15 minutes and stir the resulting mixture for 30 minutes. Then slowly raise the temperature of the solution to room temperature. Quench the reaction with 40 mL of saturated NH4Cl solution. Then extract the mixture with EtOAc, wash with salt water, dry with Na2SO4, filter, and concentrate. The residue was purified on silica gel (hexane/EtOAc, 4:1) to obtain 3-chloro-4-cyanopyridine. Light yellow needle like substance, with a yield of 937mg, 71%. Melting point 79-80 ° C. 1H NMR (400 MHz, CDCl3) δ 8.82 (s, 1H), 8.68 (d, J=4.92 Hz, 1H), 7.56 (d, J=4.84 Hz, 1H).

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