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Abdullaev, M. G.

doi:10.1023/a:1010406927727

Cited by 10 publications

(12 citation statements)

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“…The preparation and activation of the Pd-containing anion exchangers, the study methods, the hydrogenation procedure, and the isolation, purification, and identification of reaction products were described before [2,3].…”

Section: Experimental Partmentioning

confidence: 99%

Synthesis of Novocainamide by Hydrogenation of 4-Nitro-N-[2-(Diethylamino)Ethyl]Benzamide on Pd-Containing Anion Exchangers

Abdullaev

Gebekova

2015

Pharm Chem J

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The synthesis of novocainamide by hydrogenation of 4-nitro-N-[2-(diethylamino)ethyl]benzamide on Pd-containing anion exchangers was studied. An improved method for synthesizing novocainamide under mild conditions that was more efficient than the industrial method was proposed based on the experimental results. Novocainamide{4-amino-N-[2-(diethylamino)ethyl]-benzamide} (I) differs chemically from novocaine by the presence of an amide instead of an ester. Their pharmacological properties are also similar. However, I is more preferred as an antiarrhythmic because the amide is more difficultly hydrolyzed by blood plasma esterases and, as a result, has a longer duration of action. The key step in the synthesis of I is reduction of 4-nitro-N-[2-(diethylamino)ethyl]benzamide (II) [1]. The overall process efficiency depends largely on the nature of the reductant. Thus, a large amount of side products and intermediates results from incomplete reduction of the nitro group in II. Catalytic hydrogenation of II on heterogeneous catalysts is accompanied by hydrogenolysis of the amide to form its cleavage products. These drawbacks are the main reason for the reduced yield of I and the increased materials consumption during its manufacturing.We studied the hydrogenation of II in the presence of Pd-containing polymers in order to reduce the number of intermediate steps and increase the yield of I (Scheme 1). Scheme 1. Synthesis of I by hydrogenation of II on Pd-containing anion exchangers.Previous research showed [2 -4] that the amount and formation rate of products of incomplete reduction of the nitro group in the aromatic ring depended on the reaction conditions, the nature of the reductant, and the solvent.The catalysts were anion exchangers AV-17-8-Pd, AN-1-Pd, and AN-108-e-Pd that contained Pd-nanoparticle active centers that were strongly bound in the three-dimensional polymer matrices [5,6]. Preliminary studies showed that hydrogenation of II under the selected conditions was kinetically controlled and was first-order in catalyst and H 2 .

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Section: Experimental Partmentioning

confidence: 99%

Synthesis of Novocainamide by Hydrogenation of 4-Nitro-N-[2-(Diethylamino)Ethyl]Benzamide on Pd-Containing Anion Exchangers

Abdullaev

Gebekova

2015

Pharm Chem J

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“…Methods used for the preparation of catalysts, reductive acylation process, and the analysis of reaction mixtures are described elsewhere [7]. 4-Acetamidophenol (paracetamol).…”

Section: Experimental Partmentioning

confidence: 99%

“…This behavior is probably explained by a higher selectivity of the latter in the reaction of hydrogenation of nitro compounds [3,4] and by the catalytic activity of free functional groups of anion-exchange resins in the acylation of compound IV formed in situ. In addition, the organic synthesis is frequently accompanied by a rapid poisoning of Pd/C [5], whereas metal-containing polymers practically never lose their activity and selectivity [6,7].…”

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4-Aetaminophenol and 4-hydroxyphenylsalicylamide synthesized by reductive acylation of 4-nitrophenol on palladium catalysts

Abdullaev

Klyuev

2005

Pharm Chem J

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The possibility of obtaining paracetamol (4-acetamidophenol) and oxaphenamide (4-hydroxyphenylsalicylamide) by means of a single-stage reductive acylation of 4-nitrophenol on palladium catalysts has been studied. Using this single-stage reaction under mild conditions (organic solvents; temperature, 45°C; hydrogen pressure, 1 bar) the target compounds were obtained with a yield of 70 -90% for paracetamol and 41 -63% for oxaphenamide. Metal -polymer catalyst systems have proved to be more active and selective than the traditional heterogeneous Pd/C catalysts.

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“…Our accumulated experience in the synthesis of medicinal substances containing amino groups by hydrogenation [1,2], hydroamination [3], and reductive acetylation [4] on palladium catalysts allows us to obtain target products at high yield. We have investigated the potential of the catalytic synthesis of an important group of pharmaceutical agentslocal anesthetics [5]: lidocaine (a-diethylamino-2,6-dimethylacetanilide, I), bipuvacaine (1-butyl-N-(2,6-dimethylphenyl)-2-piperidinecarboxamide, II), mepivacaine (1-methyl-N-(2,6-dimethylphenyl)-2-piperidinecarboxamide, III), trimecaine (a-diethylamino-2,4,6-trimethylacetanilide, IV), and pyromecaine (1-butyl-2,4,6-trimethyl-2-pyrrolidinecarboxamide, V).…”

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“…The resulting a-picolinic acid 2,6-xylidide is methylated to form compound III by hydroamination of formalde- 1 hyde with a-picolinic acid 2,6-xylidide on Pd\C. Another method [9] produces III by the interaction of 1-methylpiperidine-2-carboxylic acid ethyl ester with 2,6-dimethylaniline magnesium bromide previously prepared from VI and ethyl magnesium bromide.…”

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Preparation of lidocaine, bipuvacaine, mepivacaine, trimecaine, and pyromecaine by reductive acylation on palladium catalysts

et al. 2008

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Cited by 10 publications

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Synthesis of Novocainamide by Hydrogenation of 4-Nitro-N-[2-(Diethylamino)Ethyl]Benzamide on Pd-Containing Anion Exchangers

Synthesis of Novocainamide by Hydrogenation of 4-Nitro-N-[2-(Diethylamino)Ethyl]Benzamide on Pd-Containing Anion Exchangers

4-Aetaminophenol and 4-hydroxyphenylsalicylamide synthesized by reductive acylation of 4-nitrophenol on palladium catalysts

Preparation of lidocaine, bipuvacaine, mepivacaine, trimecaine, and pyromecaine by reductive acylation on palladium catalysts

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