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Self-catalyzed direct amidation of ketones: A sustainable procedure for acetaminophen synthesis

Paper ID Volume ID Publish Year Pages File Format Full-Text
49571 46755 2014 6 PDF Available
Title
Self-catalyzed direct amidation of ketones: A sustainable procedure for acetaminophen synthesis
Abstract

•A procedure for fast, high yielding, one-pot aromatic amide synthesis•Hydroxylamine hydrochloride as oximation agent and rearrangement catalyst•High yield of acetaminophen is obtained at 110 °C in solventless condition.

High yielding amination of ketones and benzaldehyde in acid-less conditions has been conducted on several ketones to achieve amides and nitriles. The reactivity of the selected substrates showed to depend on both oximation and Beckmann rearrangement reaction rates. Oximation allows the in-situ production of hydrochloric acid that enables Beckmann rearrangement of the oxime to form the corresponding amide or nitrile. It is noteworthy that, using this one-pot synthetic approach, N-acetyl-4-aminophenol (acetaminophen drug), can be easily synthesized starting from 4-hydroxy-acetophenone in high yield. Acetanilide and ε-caprolactam can be also efficiently synthesized employing this synthetic procedure.

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Keywords
Acetaminophen; Amides; Self-catalyzed; Oximation; Beckmann rearrangement
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Self-catalyzed direct amidation of ketones: A sustainable procedure for acetaminophen synthesis
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Publisher
Database: Elsevier - ScienceDirect
Journal: Catalysis Communications - Volume 54, 5 September 2014, Pages 11–16
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Catalysis
Get Full-Text Now
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Price was $35.95
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Price after discount Only $4.95
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Full-text PDF Download
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