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Isonicotinic acid N-oxide (INO) is a widely used chemical intermediate in the chemical industry.
It is primarily used as a raw material for the production of various pharmaceuticals, agrochemicals, and other specialty chemicals.
The synthesis of INO involves several steps, which can be classified into two main categories: direct and indirect methods.
Direct Method
The direct method involves the oxidation of nicotinic acid (NA) to INO using sodium periodate or potassium permanganate as the oxidizing agent.
The reaction typically takes place in an aqueous medium, and the product is purified by dissolving it in water and filtering.
This method is relatively simple and cost-effective, but it requires careful control of the reaction conditions to avoid the formation of unwanted side products.
Indirect Method
The indirect method involves the conversion of NA to N-hydroxy-N,N-dimethylaminomethyl-2,6-dimethylphenylamine (HMDB:36036418), also known as dimethylphenylamine (DMPA), which is then transformed into INO through a series of chemical reactions.
The reaction sequence typically involves the following steps:
- Conversion of NA to DMPA using a reducing agent, such as lithium aluminum hydride (LiAlH4).
- Oxidation of DMPA to N-oxide using a oxidizing agent, such as chloramine T.
- Reduction of the N-oxide to INO using a reducing agent, such as (phenylphosphino)ferrocene (PPh3Fe) or tributyl tin.
Compared to the direct method, the indirect method is more complex and requires a higher degree of chemical expertise.
However, it offers greater control over the reaction conditions, and can produce a higher yield of INO with a higher level of purity.
Uses of Isonicotinic acid N-oxide
INO has a wide range of applications in various fields.
In the pharmaceutical industry, it is used as an intermediate for the synthesis of certain drugs, such as antidepressants and antipsychotics.
It is also used in the production of agrochemicals, such as herbicides and insecticides.
Additionally, INO has been used in research for its potential ability to act as a neuroprotectant and anti-inflammatory agent.
One of the most important applications of INO is in the production of the anti-epileptic drug levetiracetam (Keppra).
Levetiracetam is a widely prescribed medication for the treatment of epilepsy and other neurological disorders.
The synthesis of levetiracetam involves the use of INO as a key intermediate.
Another application of INO is in the production of certain antipsychotic drugs, such as clozapine (Clozaril) and quetiapine (Seroquel).
These drugs are used to treat schizophrenia and bipolar disorder, among other conditions.
In addition to its use in pharmaceuticals, INO is also used in the production of agrochemicals.
It is used as a raw material in the production of certain herbicides, such as imidazolinone herbicides, which are used to control weeds in agricultural fields.
INO is also used in the production of insecticides, such as neonicotinoids, which are used to control pests in crops.
Synthesis of Isonicotinic acid N-oxide
There are several methods for synthesizing INO, as mentioned above.
The direct method involves the oxidation of NA to INO using oxidizing agents, such as sodium periodate or potassium permanganate.
The reaction typically takes place in the presence of a sol