Use of Ultrasound in the Synthesis of 2-(Alkylamino)benzoic Acids in Water

Pellón, Raiza Texidor; Estévez‐Braun, Ana; Docampo, Maite L.; Martín, Ana; Ravelo, Ángel G.

doi:10.1055/s-2005-869834

Cited by 15 publications

(5 citation statements)

References 7 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Early reports concerning Ullmann reactions in water or aqueous media appeared in the early 2000s, 226,227 but it was only around the years 2006-2009 that this field saw an expansion. A discussion on previous work can be found in another review.…”

Section: Reactions In Watermentioning

confidence: 99%

Copper catalysed Ullmann type chemistry: from mechanistic aspects to modern development

et al. 2014

View full text Add to dashboard Cite

Cu-catalysed arylation reactions devoted to the formation of C-C and C-heteroatom bonds (Ullmann-type couplings) have acquired great importance in the last decade. This review discusses the history and development of coupling reactions between aryl halides and various classes of nucleophiles, focusing mostly on the different mechanisms proposed through the years. Selected mechanistic investigations are treated more in depth than others. For example, evidence in favour or against radical mechanisms is discussed. Cu(I) and Cu(III) complexes involved in the Ullmann reaction and N/O selectivity in aminoalcohol arylation are discussed. A separate section has been dedicated to the synthesis of heterocyclic rings through intramolecular couplings. Finally, recent developments in green chemistry for these reactions, such as reactions in aqueous media and heterogeneous catalysis, have also been reviewed.

show abstract

Section: Reactions In Watermentioning

confidence: 99%

Copper catalysed Ullmann type chemistry: from mechanistic aspects to modern development

et al. 2014

View full text Add to dashboard Cite

show abstract

“…In general, by using DMF the yields in the condensation of primary amines were significantly improved and the reaction time was reduced dramatically relative to those with water as the solvent. [15] For secondary amines (Table 1, Entries 1b-20b), we achieved moderate coupling yields (50-71 %); this can be ascribed to the enhanced steric hindrance of the secondary amines relative to the primary amines. In the case of secondary acyclic amines (Table 1, Entries 13b-20b), the yields obtained were higher than (51-57 %) those reported for this coupling.…”

Section: Resultsmentioning

confidence: 88%

“…In a previous publication, [15] we analyzed the influence of some parameters on the condensation of 2-chlorobenzoic acid and substituted primary alkylamines in water as the solvent to yield the corresponding 2-(alkylamino)benzoic acids. It was observed that the reaction of 3 wt.-% of copper, 2.0 equiv.…”

Section: Resultsmentioning

confidence: 99%

“…of potassium carbonate afforded, after 5 h, the corresponding 2-(alkylamino)benzoic acid with yields superior to those reported in the literature with the use of other preparative procedures. [16][17][18] We also examined the effect of ultrasonic irradiation for the synthesis of these compounds, increasing the yields in a 20 % rate after only 20 min [15] (Scheme 1). Scheme 1.…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Ultrasound‐Promoted Reaction of 2‐Chlorobenzoic Acids and Aliphatic Amines

Docampo¹,

Pellón²,

Estévez‐Braun

et al. 2007

Eur J Org Chem

View full text Add to dashboard Cite

An improvement to the use of DMF as a solvent for the condensation of 2‐chlorobenzoic acids with aliphatic primary or secondary amines was described. A number of alkylaminobenzoic acids and dialkylaminobenzoic acids were synthesized in acceptable‐to‐good yield. The advantages of this procedure include readily available substrates, the use of an inexpensive copper powder without taking any precautions to exclude moisture under mild conditions and experimental ease. Furthermore, this condensation could also be achieved under nonclassical conditions by using ultrasonic irradiation at room temperature. We demonstrated that ultrasound‐promoted condensation of 2‐chlorobenzoic acid with aliphatic amines with the use of DMF as the solvent, especially in the case of secondary amines, affords products in high yields and reduces the reaction time to minutes. The results proved to be highly reproducible because the relevant sonochemical parameters were rigorously controlled.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

show abstract

“…Robin and co-workers successfully synthesized acridine derivatives using this method (Robin, M., et al, 2002). In order to replace dry organic solution with more environmentally benign ones: Pellon et al extended the synthesis of halobenzoic acid and alkylamine in the presence of water as a solvent with copper under probe sonication (Pellon, R. F., et al, 2005 ). In most cases the yields were 20% greater than those resulting from classic heating.…”

Section: Fig (14)mentioning

confidence: 99%

Sonochemistry (Applications of Ultrasound in Chemical Synthesis and Reactions): A Review Part I

Mohamed

2016

Al-Azhar Journal of Pharmaceutical Sciences

View full text Add to dashboard Cite

Sonochemistry is a powerful and green approach which is being used to accelerate synthesis of organic compounds, and involves the use of ultrasound technique to promote chemical reactions. Ultrasound is the part of the sonic spectrum, which ranges from about 20 KHz to 10 MHz. A large number of organic reactions can be carried out under ultrasonic irradiation in high yields, short reaction times, and mild conditions. Ultrasonic irradiation of liquids causes high energy chemical reactions to occur, often with the emission of light. The origin of sonochemistry and sonoluminescence is acoustic cavitation which is the formation, growth, and implosive collapse of bubbles. The collapse of bubbles caused by cavitation produces intense local heating and high pressures, with very short lifetimes (Hot spots). These hot-spots have an equivalent temperatures of roughly 5,000 K, pressures of about 1,000 atm, and increase reactivity by nearly million-fold using the radical mechanism. A variety of devices have been used for ultrasonic irradiation of solutions.

show abstract

Use of Ultrasound in the Synthesis of 2-(Alkylamino)benzoic Acids in Water

Abstract: The synthesis of substituted 2-(alkylamino)benzoic acids using the Ullmann condensation with water as the solvent and utilizing ultrasound irradiation was achieved with high yields in a short reaction time.

Cited by 15 publications

References 7 publications

Copper catalysed Ullmann type chemistry: from mechanistic aspects to modern development

Copper catalysed Ullmann type chemistry: from mechanistic aspects to modern development

Ultrasound‐Promoted Reaction of 2‐Chlorobenzoic Acids and Aliphatic Amines

Sonochemistry (Applications of Ultrasound in Chemical Synthesis and Reactions): A Review Part I

Contact Info

Product

Resources

About