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Isonicotinic acid N-oxide, also known as oxonicotinic acid, is a pharmaceutical intermediate used in the production of certain types of antidepressant drugs.
The chemical formula for isonicotinic acid N-oxide is C8H12N2O3.
It is a white or practically white, odorless, crystalline powder that is soluble in water and slightly soluble in ethanol.
There are several synthetic routes that can be used to manufacture isonicotinic acid N-oxide, including the following:
- Hydrolysis of N-substituted Isonicotinic Acid Hydrochloride
This route involves the hydrolysis of N-substituted isonicotinic acid hydrochloride using a strong acid catalyst, such as hydrochloric acid or sulfuric acid.
The reaction typically takes place in a solvent, such as water or ethanol, and the resulting product is then purified by crystallization or chromatography. - Reduction of Isonicotinic Acid N-oxide with Lithium Aluminum Hydride (LAH)
Isonicotinic acid N-oxide can also be reduced to isonicotinic acid using lithium aluminum hydride (LAH) as a reducing agent.
The reaction takes place in the presence of a solvent, such as ether or THF, and the product is then purified using chromatography or crystallization. - Reduction of 2-Chloro-N-(2,6-dimethoxybenzyl) isonicotinamide with Hydride Donors
Another route to isonicotinic acid N-oxide involves the reduction of 2-chloro-N-(2,6-dimethoxybenzyl) isonicotinamide using hydride donors, such as lithium aluminum hydride or sodium borohydride.
The reaction takes place in the presence of a solvent, such as acetonitrile or DMF, and the resulting product is then purified by chromatography or crystallization.
In addition to these synthetic routes, isonicotinic acid N-oxide can also be synthesized using other methods, such as the Grignard reaction or the Wolff-Kishner reduction.
The specific synthetic route used will depend on the availability of starting materials and the desired yield and purity of the final product.
Isonicotinic acid N-oxide is an important intermediate in the production of certain types of antidepressant drugs, including tricyclic antidepressants and selective serotonin reuptake inhibitors (SSRIs).
It is also used in the synthesis of other pharmaceutical compounds and research chemicals.
Due to its potential for abuse and dependence, isonicotinic acid N-oxide is a controlled substance in many countries and is subject to strict regulations regarding its production, distribution, and use.
It is important for chemical manufacturers and pharmaceutical companies to adhere to these regulations and to ensure the safe handling and use of this chemical.