cas 56-91-7, 4-(Aminomethyl)benzoic acid | Articles data

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Novel preparation method of aminomethylbenzoic acid
The invention belongs to the technical field of medicines, and relates to a novel preparation method of aminomethylbenzoic acid, acetamide is adopted as a novel nitrogen source for synthesis of aminomethylbenzoic acid, the preparation method is green, environment-friendly, cheap, easy to obtain and high in safety, and specifically, ethyl p-chloromethyl benzoate is subjected to acetamide amination to obtain p-acetamidomethyl benzamide, and then hydrolysis and neutralization reactions are carried out to obtain aminomethylbenzoic acid.
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Paragraph 0021-0026

(2021/09/08)

P-aminomethyl benzoic acid and preparation method thereof
The invention discloses p-aminomethyl benzoic acid and a preparation method thereof. The method comprises the following steps: hydrolyzing phthalic anhydride as a raw material under an alkaline condition to enable the anhydride structure of phthalic anhydride to be subjected to ring opening to obtain an intermediate 1; performing decarboxylation reaction on the intermediate 1 under the condition that high-temperature liquid water is used as a reaction medium to obtain an intermediate 2; converting original binary acid of the intermediate 1 into monobasic acid, and enabling the intermediate 2 to react with a saturated monochloromethane diethyl ether solution by taking diethyl ether as a solvent under the catalytic action of aluminum chloride to obtain an intermediates 3; and carrying out bromine substitution reaction on the intermediate 3 and N-bromosuccinimide, and carrying out ammoniation reaction under the action of triethylamine and potassium carbonate. The yield of p-aminomethyl benzoic acid prepared by the preparation method of p-aminomethyl benzoic acid is high, and compared with an existing preparation method, most of the used raw materials are low-price raw materials, cyanogroups with high toxicity are not introduced, and the production cost of tranexamic acid is greatly reduced.
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Paragraph 0020; 0033-0034; 0038-0040; 0044-0046; 0049; 0057

(2020/09/09)

Preparation method of aminomethylbenzoic acid
The invention belongs to the technical field of chemical synthesis, and particularly relates to a preparation method of aminomethylbenzoic acid. The method comprises the following steps: carrying outchlorination reaction on p-toluic acid and a chlorination reagent under the condition of a catalyst I to obtain an intermediate p-chloromethylbenzoic acid, and carrying out ammonolysis on the intermediate p-chloromethylbenzoic acid and ammonia water under the condition of a catalyst II to prepare aminomethylbenzoic acid. The purity of the obtained product aminomethylbenzoic acid is greater than 99.9%, the single impurity content is less than 0.1%, and the overall yield of the two-step reaction is greater than 63%. The method is short in synthetic route, free of highly toxic reagents or precious metals, low in production cost, less in environmental pollution, high in overall yield and suitable for large-scale industrial production.
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Paragraph 0029-0032

(2020/12/29)

Method for preparing aminomethylbenzoic acid by cyclically using bromine element
The invention discloses a method for preparing aminomethylbenzoic acid by cyclically using bromine elements. The method comprises the following steps of performing bromination reaction on methyl benzoic acid and bromination agents under the existence conditions of a first catalyst and an oxidizing agent to prepare bromomethylbenzoic acid; then, performing ammonolysis by ammonium hydroxide under the existence of the first catalyst to obtain a product of aminomethylbenzoic acid; recovering bromine-containing master batch generated by bromination reaction and ammonolysis reaction by separation, distillation and filtering methods. The yield of the product of aminomethylbenzoic acid is not lower than 96 percent after recrystallization; the product purity is 99 percent; the bromine element is contained in the bromination agents; the bromination agents are selected from hydrogen bromide and acidic bromine-containign solution. The yield and the purity of the aminomethylbenzoic acid prepared bythe method are high; in addition, the bromine element and the ammonium hydroxide in the reaction system can be cyclically used; the production cost is reduced.
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Paragraph 0048-0084

(2019/07/01)

Synthetic method for aminomethylbenzoic acid
The invention discloses a synthetic method for aminomethylbenzoic acid. The synthetic method specifically comprises the following steps: adding 4-halomethyl alkyl benzoate and triethylamine, dropwiseadding ethanol-water solution in which 2-amino-5-methyl-1,3,4-thiadiazole is dissolved while stirring, after a reaction is completed, evaporating solution until a lot of solids are separated out, cooling, filtering, and drying to obtain 4-aminomethyl alkyl benzoate; adding the 4-aminomethyl alkyl benzoate to acid solution, reacting by stirring, cooling, adding water, and dropwise adding alkali until the solution is alkaline, and a lot of the solids are separated out, filtering, washing, and drying to obtain the aminomethylbenzoic acid. The synthetic method is moderate in reaction conditions, less in side reactions, high in yield, low in cost, short in reaction and post-processing time, low in energy consumption, high in production efficiency, small in environmental pollution, and simple in'three wastes' treatment, and suitable for the industrial production. -CN with strong toxicity and an organic solvent with strong pollution are not used, and reaction raw materials are cheap in priceand easy to obtain.
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Paragraph 0040; 0042; 0043; 0045; 0046; 0048; 0053

(2018/11/22)

An improved and practical synthesis of tranexamic acid
Tranexamic acid 1, a synthetic antifibrinolytic drug with the treatment being considered highly cost-effective in many countries, has been included in the WHO list of essential medicines. In this paper, we designed the synthesis of 1 via a novel seven-step route from the readily available starting material dimethyl terephthalate, performing with 99.6% purity in 59.2% overall yield. During the process, we successfully developed a direct and efficient method for the preparation of key intermediate methyl 4-(acetamidomethyl)benzoate by one-pot hydrogenation and acylation in acetic anhydride using Ni/Al2O3 as a catalyst. More importantly, it should be a straightforward and practical way to circumvent the usage of toxic reagents (CrO3, Cl2), solvent (CCl4), and expensive catalyst (PtO2), etc., that plagued the previous methodologies.
Li, Zhenhua,Fang, Li,Wang, Jian,Dong, Liuhong,Guo, Yanna,Xie, Yuanyuan
p. 444 - 448
(2015/03/30)

Immunomodulatory peptides
The invention relates to peptides derivatized with a hydrophilic polymer which, in some embodiments, bind to human FcRn and inhibit binding of the Fc portion of an IgG to an FcRn, thereby modulating serum IgG levels. The disclosed compositions and methods may be used in some embodiments, for example, in treating autoimmune diseases and inflammatory disorders. The invention also relates, in further embodiments, to methods of using and methods of making the peptides of the invention.
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(2014/12/12)

Substrate profile of an ω-transaminase from Burkholderia vietnamiensis and its potential for the production of optically pure amines and unnatural amino acids
A new (S)-enantioselective ω-transaminase (ω-TA) gene from Burkholderia vietnamiensis G4 was functionally expressed in Escherichia coli BL21 (DE3), and the purified recombinant N-terminal His-tagged ω-TA (HBV-ω-TA) had a dimeric structure with optimum pH and temperature of 8.4 and 40 C, respectively. The enzyme showed higher activities toward aromatic amines than aliphatic amines and (S)-1-methylbenzylamine ((S)-α-MBA) was the most active amino donor. For amino acceptor, keto acids, keto esters and aldehydes were more reactive than ketones with pyruvate ethyl ester being most active. Several chiral amines and unnatural amino acids or esters were synthesized using HBV-ω-TA as the catalyst and isopropylamine or (S)-α-MBA as amino donor. Notably, HBV-ω-TA catalyzed the amino transfer to β-keto esters to give optically pure β-amino acid esters. In addition, glyoxylate was used as amino acceptor for the first time in the kinetic resolution of racemic amines and optically pure amines, such as (R)-1-methylbenzylamine, (R)-1-phenylpropylamine, (R)-2-amino-4-phenylbutane and (R)-1-aminotetraline, were obtained.
Jiang, Jinju,Chen, Xi,Feng, Jinhui,Wu, Qiaqing,Zhu, Dunming
p. 32 - 39
(2014/01/06)

PREPARATION METHOD OF 4-AMINOMETHYLBENZOIC ACID
The present invention relates to a preparation method of 4-aminomethylbenzoic acid comprising the following steps: preparing 4-carboxylbenzaldehyde or an alkyl ester thereof (methyl 4-formyl benzoate); reacting the 4-carboxylbenzaldehyde or an alkyl ester thereof (methyl 4-formyl benzoate) with hydroxyamine to oximate the same; and contact reducing 4-carboxylbenzaldehyde oxime or an alkyl ester oxime thereof obtained by the oximation, through hydrogen in a sodium hydroxide aqueous solution. Since methyl 4-hydroxyiminomethylbenzoate is reacted as a raw material in the presence of an alkali, hydrogen of a relatively low pressure can be used and a purification process is also simple, thereby enabling preparation of 4-aminomethylbenzoic acid with a low cost and high yield.
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Page/Page column 5-6

(2012/12/13)

PREPARATION METHOD OF 4-AMINOMETHYLBENZOIC ACID
The present invention relates to a preparation method of 4-aminomethylbenzoic acid comprising the following steps: preparing 4-carboxylbenzaldehyde or an alkyl ester thereof (methyl 4-formyl benzoate); reacting the 4-carboxylbenzaldehyde or an alkyl ester thereof (methyl 4-formyl benzoate) with hydroxyamine to oximate the same; and contact reducing 4-carboxylbenzaldehyde oxime or an alkyl ester oxime thereof obtained by the oximation, through hydrogen in a sodium hydroxide aqueous solution. Since methyl 4-hydroxyiminomethylbenzoate is reacted as a raw material in the presence of an alkali, hydrogen of a relatively low pressure can be used and a purification process is also simple, thereby enabling preparation of 4-aminomethylbenzoic acid with a low cost and high yield.
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Page/Page column 4

(2012/12/13)

Benzothiazole Formulations and Use Thereof
The present invention is related to macrogol glyceride pharmaceutical formulations containing benzothiazole derivatives. In particular, the invention is related to benzothiazole stearoyl macrogol pharmaceutical formulations, method of preparation and use thereof.
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Page/Page column 23

(2010/11/30)

Arylalkylamine vanadium (V) salts for the treatment and/or prevention of Diabetes mellitus
This invention provides compounds of formula (IIA) and pharmaceutical compositions thereof, where M, a, b, and R1-R5 are as defined herein, for treating human type 1 and type 2 diabetes, particularly insulin-resistant diabetes. Pharmaceutical compositions comprising the compounds of formula (IIA) are also disclosed.
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Page/Page column 19; 20

(2010/11/26)

BASIC AMINE COMPOUND AND USE THEREOF
Novel amine compounds which are represented by the following formula (1) and efficacious against diseases such as a viral infectious disease with HIV, rheumatism, and cancer metastasis; typically, A 1 and A 2 represent a hydrogen atom or a substitutable monocyclic or polycyclic heteroaromatic ring and W represents a substitutable benzene ring or any group represented by the following formula (10) or (11): where X represents O, CH 2 , C(=O), NR 11 , or CHR 35 and D represents a group represented by the following formula (6): where Q represents a single bond, NR 12 , or a group represented by the formula (13): and Y represents a group represented by the following formula (7) : where z represents a substitutable monocyclic or polycyclic aromatic ring; and B represents -NR 25 R 26 ; and R 1 to R 26 in the above formulae represent a hydrogen atom, an alkyl group, an alkenyl group, or an alkynyl group.
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Page/Page column 24

(2010/11/24)

New efficient substrates for semicarbazide-sensitive amine oxidase/VAP-1 enzyme: Analysis by SARs and computational docking
Structure activity relationships for semicarbazide-sensitive amine oxidase/vascular adhesion protein-1 (SSAO/VAP-1) were studied using a library of arylalkylamine substrates, with the aim of contributing to the discovery of more efficient SSAO substrates. Experimental data were contrasted with computational docking studies, thereby allowing us to examine the mechanism and substrate-binding affinity of SSAO and thus contribute to the discovery of more efficient SSAO substrates and provide a structural basis for their interactions. We also built a model of the mouse SSAO structure, which provides several structural rationales for interspecies differences in SSAO substrate selectivity and reveals new trends in SSAO substrate recognition. In this context, we identified novel efficient substrates for human SSAO that can be used as a lead for the discovery of antidiabetic agents.
Yraola, Francesc,García-Vicente, Silvia,Fernández-Recio, Juan,Albericio, Fernando,Zorzano, Antonio,Marti, Luc,Royo, Miriam
p. 6197 - 6208
(2007/10/03)

Non-hygroscopic crystals of p-aminomethylbenzoic acid and process for preparing the same
The novel non-hygroscopic crystals of p-aminomethylbenzoic acid can be obtained by heating hygroscopic crystals of p-aminomethylbenzoic acid with keeping the hygroscopic crystals in contact with moisture to transit the hygroscopic crystals to non-hygroscopic crystals. The non-hygroscopic crystals of p-aminomethylbenzoic acid can be particularly advantageously handled in the atmosphere as compared with the conventional hygroscopic crystals. Especially when the p-aminomethylbenzoic acid is used for the non-aqueous reaction, the crystals of the invention are exceptionally advantageous from the viewpoints of removal of moisture and humidity control.
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(2008/06/13)

Prodrug derivatives of carboxylic acid drugs
Novel ester derivatives of carboxylic acid medicaments of formula (I), wherein R--COO--represents the acyloxy residue of a carboxylic acid drug or medicament, n is an integrer from 1 to 3, and R1 and R2 are the same or different and are selected from a group consisting of an alkyl, an alkenyl, an aryl, an aralkyl, a cycloalkyl and which group may be unsubstituted or substituted, or R1 and R2 together with the N forms a 4-, 5-, 6- or 7-membered heterocyclic ring, which in addition to the nitrogen atom may contain one or two further heteroatoms selected from the group consisting of nitrogen, oxygen and sulfur and which heterocyclic group may be substituted. These compounds are highly biolabile prodrug forms of the corresponding carboxylic acid compounds and are highly susceptible to undergoing enzymatic hydrolysis in vivo whereas they are highly stable in aqueous solution. The novel derivatives are less irritating to mucosa than the parent carboxylic acids and may provide an improved bio-availability of the drugs.
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(2008/06/13)