4‐Monoalkylierte Aminoantipyrine

Skita, A.; Keil, Frerich J.; Stühmer, Werner

doi:10.1002/cber.19420751241

Cited by 7 publications

(4 citation statements)

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“…Group 9 (Co, Rh, Ir) Metal-Catalyzed Reductive Amination Co. As early as 1942, Skita and co-workers demonstrated the monoalkylation of 4-aminoantipyrine with propionaldehyde at 4.3 bar H 2 and room temperature using a Co catalyst supported on diatomaceous earth (Scheme 11). 41 Many years later, in 2014, Beller and co-workers published a well-defined Co-based catalyst (Co 3 O 4 /NGr@C) for the domino reductive amination of carbonyl compounds with nitroarenes (Scheme 12A). 42 The catalyst was prepared by pyrolysis of [Co(OAc) 2 ] and 1,10-phenanthroline on Vulcan XC72R as a carbon support at 800 °C under inert conditions.…”

Section: Reductive Amination Using Heteregeneous Transition Metal Cat...mentioning

confidence: 99%

“…The synthesis of 4-monoalkylated aminoantipyrines, interesting for its hydrotropic and analgesic effects, starting from 4amino-, 4-nitro-, and 4-nitroso-antipyrines and aldehydes or ketones in different molar ratios was demonstrated by Skita's group in 1942 (Scheme 80). 41 A total of 15 examples could be synthesized in up to quantitative yields using a Pt-BaSO 4 catalyst at 3.9−4.3 bar H 2 .…”

Section: Reductive Amination Using Heteregeneous Transition Metal Cat...mentioning

confidence: 99%

“…The monoalkylation of 4-aminoantipyrine with acetone using a Ni catalyst supported on silica (Ni-silica) was demonstrated by Skita and co-workers in 1942 (Scheme ). Quantitative formation of the product was observed after 2 h at 50.01 bar H 2 and 90 °C.…”

Section: Reductive Amination Using Heteregeneous Transition Metal Cat...mentioning

confidence: 99%

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Transition-Metal-Catalyzed Reductive Amination Employing Hydrogen

2020

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The reductive amination, the reaction of an aldehyde or a ketone with ammonia or an amine in the presence of a reducing agent and often a catalyst, is an important amine synthesis and has been intensively investigated in academia and industry for a century. Besides aldehydes, ketones, or amines, starting materials have been used that can be converted into an aldehyde or ketone (for instance, carboxylic acids or organic carbonate or nitriles) or into an amine (for instance, a nitro compound) in the presence of the same reducing agent and catalyst. Mechanistically, the reaction starts with a condensation step during which the carbonyl compound reacts with ammonia or an amine, forming the corresponding imine followed by the reduction of the imine to the alkyl amine product. Many of these reduction steps require the presence of a catalyst to activate the reducing agent. The reductive amination is impressive with regard to the product scope since primary, secondary, and tertiary alkyl amines are accessible and hydrogen is the most attractive reducing agent, especially if large-scale product formation is an issue, since hydrogen is inexpensive and abundantly available. Alkyl amines are intensively produced and use fine and bulk chemicals. They are key functional groups in many pharmaceuticals, agro chemicals, or materials. In this review, we summarize the work published on reductive amination employing hydrogen as the reducing agent. No comprehensive review focusing on this subject has been published since 1948, albeit many interesting summaries dealing with one or the other aspect of reductive amination have appeared. Impressive progress in using catalysts based on earth-abundant metals, especially nanostructured heterogeneous catalysts, has been made during the early development of the field and in recent years.

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Section: Reductive Amination Using Heteregeneous Transition Metal Cat...mentioning

confidence: 99%

Section: Reductive Amination Using Heteregeneous Transition Metal Cat...mentioning

confidence: 99%

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Transition-Metal-Catalyzed Reductive Amination Employing Hydrogen

2020

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“…Based on the inspiring development of Co catalysts for the selective hydrogenation of nitriles, [25–30] we expected that a Co catalyst could also be the key to develop a broadly applicable catalytic process for the reductive alkylation of nitriles. Co catalysts have also been employed successfully in reductive amination reactions, the coupling of amines or ammonia and aldehydes or ketones in the presence of hydrogen as the reducing agent [27, 31–41] . In addition, the Co catalyzed transfer hydrogenation and coupling of nitriles has been described [42] …”

Section: Methodsmentioning

confidence: 99%

General Synthesis of Secondary Alkylamines by Reductive Alkylation of Nitriles by Aldehydes and Ketones

Schönauer

Thomä

Kaiser

et al. 2020

Chemistry A European J

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The development of C−N bond formation reactions is highly desirable due to their importance in biology and chemistry. Recent progress in 3d metal catalysis is indicative of unique selectivity patterns that may permit solving challenges of chemical synthesis. We report here on a catalytic C−N bond formation reaction—the reductive alkylation of nitriles. Aldehydes or ketones and nitriles, all abundantly available and low‐cost starting materials, undergo a reductive coupling to form secondary alkylamines and inexpensive hydrogen is used as the reducing agent. The reaction has a very broad scope and many functional groups, including hydrogenation‐sensitive examples, are tolerated. We developed a novel cobalt catalyst, which is nanostructured, reusable, and easy to handle. The key seems the earth‐abundant metal in combination with a porous support material, N‐doped SiC, synthesized from acrylonitrile and a commercially available polycarbosilane.

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The Preparation of Amines by Reductive Alkylation

Emerson

2011

Organic Reactions

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Reductive alkylation is the term applied to the process of introducing alkyl groups into ammonia or primary or secondary amine by means of an aldehdye or ketone in the presence of a reducing agent. This chapter is limited to those reductive alkylations in which the reducing agent is hydrogen and a catalysts or nascent hydrogen, usually from a metal‐acid combination; most of these reductive alkylations have been carried out with hydrogen and a catalyst.

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4‐Monoalkylierte Aminoantipyrine

Cited by 7 publications

References 0 publications

Transition-Metal-Catalyzed Reductive Amination Employing Hydrogen

Transition-Metal-Catalyzed Reductive Amination Employing Hydrogen

General Synthesis of Secondary Alkylamines by Reductive Alkylation of Nitriles by Aldehydes and Ketones

The Preparation of Amines by Reductive Alkylation

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