One-step reductive amidation of nitro arenes: application in the synthesis of Acetaminophen™

Bhattacharya, Apurba; Purohit, Vikram C.; Suarez, Victor H.; Tichkule, Ritesh; Parmer, Gaurang; Rinaldi, Frank

doi:10.1016/j.tetlet.2005.09.196

Cited by 48 publications

(34 citation statements)

References 18 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Synthesis of lidocaine (a local anesthetic) is a classic organic chemistry laboratory exercise that starts with the reduction of 2,6-dimethylnitrobenzene to 2,6-xylidine. Paracetamol, also known as acetaminophen, which is sold as an over-the-counter analgesic and antipyretic, is produced in a one-step reductive acetamidation of p-nitrophenol (8).…”

Section: Synthetic Nitroaromatic Compoundsmentioning

confidence: 99%

Nitroaromatic Compounds, from Synthesis to Biodegradation

Parales

2010

Microbiol Mol Biol Rev

775

470

View full text Add to dashboard Cite

SUMMARY Nitroaromatic compounds are relatively rare in nature and have been introduced into the environment mainly by human activities. This important class of industrial chemicals is widely used in the synthesis of many diverse products, including dyes, polymers, pesticides, and explosives. Unfortunately, their extensive use has led to environmental contamination of soil and groundwater. The nitro group, which provides chemical and functional diversity in these molecules, also contributes to the recalcitrance of these compounds to biodegradation. The electron-withdrawing nature of the nitro group, in concert with the stability of the benzene ring, makes nitroaromatic compounds resistant to oxidative degradation. Recalcitrance is further compounded by their acute toxicity, mutagenicity, and easy reduction into carcinogenic aromatic amines. Nitroaromatic compounds are hazardous to human health and are registered on the U.S. Environmental Protection Agency's list of priority pollutants for environmental remediation. Although the majority of these compounds are synthetic in nature, microorganisms in contaminated environments have rapidly adapted to their presence by evolving new biodegradation pathways that take advantage of them as sources of carbon, nitrogen, and energy. This review provides an overview of the synthesis of both man-made and biogenic nitroaromatic compounds, the bacteria that have been identified to grow on and completely mineralize nitroaromatic compounds, and the pathways that are present in these strains. The possible evolutionary origins of the newly evolved pathways are also discussed.

show abstract

Section: Synthetic Nitroaromatic Compoundsmentioning

confidence: 99%

Nitroaromatic Compounds, from Synthesis to Biodegradation

Parales

2010

Microbiol Mol Biol Rev

775

470

View full text Add to dashboard Cite

show abstract

“…9 (D) Bhattacharya and co-workers reported a thioacetate-mediated one-step reductive acetamidation of aryl nitro compounds. 10 The reaction could be performed without solvent in the presence of a catalytic amount of surfactant. (E) S-Acetylarene thiols were synthesized from the corresponding aromatic amines via non-aqueous diazotization and further reaction with potassium thioacetate.…”

Section: Abstractsmentioning

confidence: 99%

Potassium Thioacetate

Soria‐Castro

2012

Synlett

View full text Add to dashboard Cite

show abstract

“…It is important to note that synthesis of paracetamol simple and can be done in the laboratory by nitrating phenol with sodium nitrate, separating the desired p-nitrophenol from the orthobyproduct, and reducing the nitro group with sodium borohydride. The resultant p-aminophenol can be acetylated with acetic anhydride (in this reaction, phenol is strongly activating, thus the reaction only requires mild conditions) to form the final product (Bhattacharya et al, 2006). The increasing importance of metal coordination complexes in the design and discovery of novel of drugs led to the heightened interest of many scientist to study metal drug complexes as lead compounds (Farrell, 1989;Kimura, 1986;Mewis and Archibald, 2010).…”

Section: Introductionmentioning

confidence: 99%

Copper-paracetamol complexes: Promising lead antibacterial drug candidates

Adadey¹,

Sarfo²

2016

Afr. J. Pure Appl. Chem.

View full text Add to dashboard Cite

Antibiotic resistance by microorganisms has triggered the need to discover new antibiotics to replace the old ones. The study was designed to prepare copper-paracetamol complexes which will serve as lead compounds towards the discovery of novel antibiotics. Copper sulphate was reacted with paracetamol in the presence of sodium nitrate in borate buffer to give products which were separated into three layers when extracted with a set of organic solvents. The topmost, third layer was separated and further washed with 1:1:1 petroleum ether, ethanol and benzene to obtain a yellow extract. The first and second layers were also air dried to obtain products 1 and 2. The maximum wavelength of absorption of products 1, 2, yellow extract and paracetamol were 250, 350, 280 and 300 nm respectively. The infrared absorption peaks suggested that, the metal coordination products formed were different from the reactants (paracetamol and cupper). The atomic absorption spectra of the extracts further indicated the association of copper with paracetamol to form the coordination complexes. Products 1, 3 and the yellow extract inhibited E. coli and staphylococcus growth. In all four products were separated and their possible structures have been proposed in the text.

show abstract

One-step reductive amidation of nitro arenes: application in the synthesis of Acetaminophen™

Cited by 48 publications

References 18 publications

Nitroaromatic Compounds, from Synthesis to Biodegradation

Nitroaromatic Compounds, from Synthesis to Biodegradation

Potassium Thioacetate

Copper-paracetamol complexes: Promising lead antibacterial drug candidates

Contact Info

Product

Resources

About