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Related Concept Videos

Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

3.4K
Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
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Preparation of Nitriles01:12

Preparation of Nitriles

2.0K
One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...
2.0K
Preparation of Carboxylic Acids: Hydrolysis of Nitriles01:19

Preparation of Carboxylic Acids: Hydrolysis of Nitriles

3.8K
Nitriles (R–CN) can be converted into carboxylic acids (R–COOH) upon treatment with aqueous acids, i.e., upon hydrolysis of nitriles. Under base-catalyzed conditions, carboxylate anions (R–COO−) are formed.
3.8K
2° Amines to N-Nitrosamines: Reaction with NaNO201:20

2° Amines to N-Nitrosamines: Reaction with NaNO2

4.0K
Secondary amines react with nitrous acid to form N-nitrosamines, as depicted in Figure 1. Nitrous acid, a weak and unstable acid, is formed in situ from an aqueous solution of sodium nitrite and strong acids, such as hydrochloric acid or sulfuric acid, in cold conditions. In the presence of an acid, the nitrous acid gets protonated. The subsequent loss of water results in the formation of the electrophile known as nitrosonium ion.
4.0K
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview01:07

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

3.1K
In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
3.1K
Nitriles to Carboxylic Acids: Hydrolysis01:08

Nitriles to Carboxylic Acids: Hydrolysis

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Nitriles undergo acid-catalyzed hydrolysis or base-catalyzed hydrolysis to form a carboxylic acid. These reactions proceed via an amide intermediate.
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Related Experiment Video

Updated: May 15, 2025

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
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Continuous Flow Synthesis of Nitrofuran Pharmaceuticals Using Acetyl Nitrate.

Hubert Hellwig1, Loïc Bovy1, Kristof Van Hecke2

  • 1Center for Integrated Technology and Organic Synthesis (CiTOS), MolSys Research Unit, University of Liège, B6a, Room 3/19, Allée du Six Août 13, Liège (Sart Tilman), B-4000, Belgium.

Angewandte Chemie (International Ed. in English)
|April 7, 2025
PubMed
Summary

A new continuous flow platform safely generates acetyl nitrate for nitrating furfural to nitrofurfural. This method improves yields and reproducibility for synthesizing key antimicrobial nitrofuran pharmaceuticals.

Keywords:
Flow chemistryFurfuralNitration platformsNitrofuransProcess analytical technology

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A General Method for Detecting Nitrosamide Formation in the In Vitro Metabolism of Nitrosamines by Cytochrome P450s
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Area of Science:

  • Organic Chemistry
  • Chemical Engineering
  • Pharmaceutical Synthesis

Background:

  • Nitrofurfural is essential for synthesizing antimicrobial nitrofuran drugs.
  • Traditional furfural nitration methods use harsh conditions, leading to low yields and poor reproducibility.
  • Existing methods for acetyl nitrate, a milder nitrating agent, are incompatible with furfural and pose safety risks.

Purpose of the Study:

  • To develop a safe and robust continuous flow platform for the nitration of furfural.
  • To address the limitations of conventional acetyl nitrate preparation and its associated safety concerns.
  • To enable efficient synthesis of nitrofurfural and related pharmaceutical intermediates.

Main Methods:

  • In situ generation of acetyl nitrate within a continuous flow reactor.
  • Automated and integrated platform for remote process operation.
  • Nitration of furfural to nitrofurfural using the developed flow system.

Main Results:

  • Successful synthesis of nitrofurfural with high reproducibility and favorable metrics.
  • Demonstrated efficiency in producing various best-selling nitrofuran pharmaceuticals, including nifuroxazide, nifurtimox, nitrofurantoin, and nitrofural.
  • Achieved excellent isolated yields for target compounds in under five minutes.

Conclusions:

  • The developed continuous flow platform offers a safe, efficient, and robust method for synthesizing nitrofurfural.
  • This approach overcomes the challenges associated with traditional nitration methods and acetyl nitrate preparation.
  • The platform facilitates the streamlined production of vital nitrofuran-based active pharmaceutical ingredients.