5434-02-6

Upstream product

• 18271-18-6 N-(2-naphthyl)-p-toluenesulphonamide 
• 7697-37-2 nitric acid 
• 64-19-7 acetic acid 
• 858005-66-0 N-(1-iodo-[2]naphthyl)-toluene-4-sulfonamide 
• 91-59-8 naphthalen-2-ylamine 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 36794-05-5 N-(1-amino-[2]naphthyl)-N-methyl-toluene-4-sulfonamide 
• 93259-31-5 N-(3-bromo-1-nitro-[2]naphthyl)-toluene-4-sulfonamide 
• 861518-31-2 N-methyl-N-(1-nitro-[2]naphthyl)-toluene-4-sulfonamide 

Relevant academic research and scientific papers

Direct oxidative nitration of aromatic sulfonamides under mild conditions

A direct nitration of aromatic sulfonamides using sodium nitrite as the nitrating agent has been developed. The reaction shows typically mono-substitution selectivity and can be enlarged to the gram scale with good yield.

Copper-catalyzed mild nitration of protected anilines

A practical copper-catalyzed direct nitration of protected anilines, by using one equivalent of nitric acid as the nitrating agent, has been developed. This procedure features mild reaction conditions, wide structural scope (with regard to both N-protecting group and arene substitution), and high functional-group tolerance. Dinitration with two equivalents of nitric acid is also feasible. Practical and reliable: A Cu-catalyzed selective nitration of para- and ortho-substituted aniline derivatives by using one equivalent of HNO3 has been developed that produces water as the only stoichiometric byproduct (see scheme; PG=protecting group). This method is compatible with strongly electron-deficient substrates, enabling dinitration (by using 2.0 equiv of HNO3). This method allows for a rapid access to relevant nitrogen-containing heterocyclic architectures.