Obtaining amines from nitrocompounds through an effective, economical and sustainable process

New and innovative aspects

In the literature, there are a wide variety of methods that allow the transformation of the nitro group (1) to an amine (2). Given the importance of these last compounds in the pharmaceutical and chemical industries, the methodology described by the researchers from the University of Burgos represents a fast, simple and cheap way to obtain amines. On the other hand, the reaction conditions are compatible with a wide variety of functional groups, even those that can be reduced. Another of the innovative aspects of this synthetic strategy is the use of γ-terpinene as a reducing agent and a dioxomolybdenum (VI) catalyst.

Main advantages of its use

The main advantages derived from the use of this methodology are:
- Obtaining the final compounds with yields ranging from 50 to 95%.
- High tolerance to other functional groups such as carbonyl groups, nitriles, unsaturated chains, etc.
- γ-Terpinene is a natural product from biomass. When used as a reducing agent, in the presence of the dioxomolybdenum (VI) catalyst, the reduction of the nitro group to an amine is achieved, forming easily separable reaction by-products.
- The transformation does not require an inert atmosphere or high pressure, which is an advantage from an economic, environmental and safety point of view.

Specifications

γ-Terpinene acts as a reducing agent, in equimolar amounts, and dimethylacetamide is used as a solvent. The dioxomolybdenum (VI) compound, MoO2Cl2(dmf)2, is added in catalytic amounts (5 mol%) and can be easily prepared from commercial reagents.
Using microwave heating, the reaction is complete in 60 minutes. Furthermore, the transformation can be carried out in the absence of solvent.
The by-products obtained in the reaction are p-cymene and water, which allows the purification of the deoxygenated product in a simple and fast way, without the need to resort to complex separation techniques.

Applications

This technology has direct application in the chemical industry and the pharmaceutical industry.

Intellectual property status

Protected by a patent P202330202

Current development status

Prototype available for demonstration.

Desired business relationship

Trade Agreement, License Agreement, Technical cooperation: further development, Technical Cooperation: testing of new applications; Technical Cooperation: adaptation to specific needs.