53405-05-3

Usage

Uses

Used in Pharmaceutical Industry:
Methyl 4-formamidobenzoate is used as a synthetic reagent for the preparation of tetrahydroisoquinoline derivatives. These derivatives hold significant importance in the pharmaceutical field, particularly as inhibitors of coagulation factor XIa. By targeting this factor, these derivatives can potentially be used in the development of treatments for conditions related to blood clotting and coagulation disorders.
The role of methyl 4-formamidobenzoate in the synthesis of these pharmaceutically relevant compounds highlights its importance as a key building block in the development of novel therapeutic agents. Its application in the pharmaceutical industry underscores the potential for further research and development in this area, as well as the need for efficient and sustainable methods of production to meet the growing demand for these compounds.

Upstream product

• 619-50-1 4-nitrobenzoic acid methyl ester 
• 16712-16-6 ammonium formate 
• 68-12-2 N,N-dimethyl-formamide 
• 619-45-4 4-methoxycarbonyl aniline 
• 64-18-6 formic acid 
• 63450-84-0 methyl 4-aminobenzoate hydrochloride 
• 124-38-9 carbon dioxide 
• 150-13-0 4-amino-benzoic acid 
• 113388-44-6 (formyloxy)(acetoxy)phenylmethane 
• 1384477-13-7 methyl 4-[(1H-imidazol-1-ylcarbonyl)amino]benzoate 
• 23138-53-6 methyl 4-isocyanatobenzoate 
• 77287-34-4 formamide 
• 2258-42-6 formyl acetic anhydride 
• 99768-12-4 4-methoxycarbonylphenylboronic acid 

Downstream Products

• 15999-36-7 Kohlensaeure-N-p-methoxycarbonylphenyl-dichloridimid 
• 160350-46-9 4-(Formyl-trimethylsilanylmethyl-amino)-benzoic acid methyl ester 
• 887577-52-8 2-(N-formyl-p-methoxycarbonylanilino)acetic acid 
• 198476-21-0 4-methoxycarbonyl-1-isocyanobenzene 

Relevant academic research and scientific papers

CuICuIIand AgI: P -isocyanobenzoates as novel 1D semiconducting coordination oligomers

Two novel semiconducting coordination oligomers with 1D chain structures, namely [H0.07 CuI0.65CuII0.14(μ-p-CNC6H4CO2)·0.9H2O]n and [Ag(μ-p-CNC6H4CO2)]n, were obtained and characterized by XRD powder patterns, and XPS, EPR, UV-vis-NIR, IR and Raman spectroscopy. According to XRD analysis, CuICuII-ICNBA is an amorphous solid, while AgI-ICNBA crystalizes with a monoclinic unit cell in the C2/c space group (Z = 4). The composition and further information of CuICuII-ICNBA were obtained from the spectroscopic data. In correspondence with the quantification of terminal groups from high-resolution XPS spectra, CuICuII-ICNBA and AgI-ICNBA are composed of an average of 9 and 7 monomer units, respectively, resulting in 1D-oligomers. The spectroscopic evidence indicates that CuICuII-ICNBA is better described as a non-stoichiometric coordination oligomer (where non-integer ratios of metal ions can be accommodated), while AgI-ICNBA is stoichiometric. In both materials, each metal center is linked by two μ-η1:η1-p-isocyanobenzoate ligands forming microfibers of around 120 nm (CuICuII-material) and 310 nm (AgI-material) in average diameters with optical band gaps of 2.60 eV and 2.17 eV, respectively.

Tetracoordinate borates as catalysts for reductive formylation of amines with carbon dioxide

We report sodium trihydroxyaryl borates as the first robust tetracoordinate organoboron catalysts for reductive functionalization of CO2. These catalysts, easily synthesized from condensing boronic acids with metal hydroxides, activate main group element-hydrogen (E-H) bonds efficiently. In contrast to BX3 type boranes, boronic acids and metal-BAr4 salts, under transition metal-free conditions, sodium trihydroxyaryl borates exhibit high reactivity of reductive N-formylation toward a variety of amines (106 examples), including those with functional groups such as ester, olefin, hydroxyl, cyano, nitro, halogen, MeS-, ether groups, etc. The over-performance to catalyze formylation of challenging pyridyl amines affords a promising alternative method to the use of traditional formylation reagents. Mechanistic investigation supports electrostatic interactions as the key for Si/B-H activation, enabling alkali metal borates as versatile catalysts for hydroborylation, hydrosilylation, and reductive formylation/methylation of CO2.

A more sustainable and highly practicable synthesis of aliphatic isocyanides

Synthesis protocols to convert N-formamides into isocyanides using three different dehydration reagents (i.e. p-toluenesulfonyl chloride (p-TsCl), phosphoryl trichloride (POCl3) and the combination of triphenylphosphane (PPh3) and iodine) were investigated and optimized, while considering the principles of green chemistry. Comparison of the yield and the E-factors of the different synthesis procedures revealed that, in contrast to the typically applied POCl3 or phosgene derivatives, p-TsCl was the reagent of choice for non sterically demanding aliphatic mono- or di-N-formamides (yields up to 98% and lowest E-factor 6.45). Apart from a significantly reduced E-factor, p-TsCl is cheap, offers a simplified reaction protocol and work-up, and is less toxic compared to other dehydration reagents. Thus, this procedure offers easier and greener access to aliphatic isocyanide functionalities.

Catalyst-Free Transamidation of Aromatic Amines with Formamide Derivatives and Tertiary Amides with Aliphatic Amines

A simple catalyst- and promoter-free protocol has been developed for the transamidation of weakly nucleophilic aromatic amines with formamide derivatives and low-reactivity tertiary amides with aliphatic amines. This strategy is advantageous because no catalyst or promoters are needed, no additives are required, separation and purification is easy, and the reaction is scalable. Significantly, this strategy was further applied to synthesize several pharmaceutical molecules on a gram scale, and excellent yields were achieved.

One-pot selective N-formylation of nitroarenes to formamides catalyzed by core-shell structured cobalt nanoparticles

One-pot direct N-formylation of readily available nitroarenes with ammonium formate catalyzed by core-shell structured cobalt nanoparticles has been developed. A broad set of nitroarenes was successfully converted to their corresponding formamides in good to high yields with various functional group tolerance. This heterogeneous catalyst can be easily removed from the reaction medium and can be reused several times without a significant loss of reaction efficiency.

Method of N-formylating amines with a phosphonic anhydride

A method for N-formylating an amine that includes reacting the amine and a formamide compound in the presence of a phosphonic anhydride to form an N-formylated amine. The phosphonic anhydride is present in an amount of 5-100 mol % relative to a total number of moles of the amine, and the reacting is performed for 1-24 hours at a temperature of 45-100° C.

Synthesis of reversed C-glycopeptide mimics monomer from galactose via passerini reaction

C-glycopeptidomimetics are formed by the condensation of sugar unit and analogues of amino acid residue which generates a new carbon-carbon sigma bond. In glycopeptides, this condensation occurs in side chain of amino acid but introduction of isonitrile moiety on N-terminal of amino acid mimic unit can also be a route to produce such compounds. It is observed that C-glycopeptidomimetics are more stable than their N- and O-analogues under physiological conditions but their synthesis is a challenging task due to relatively less reactive C-6 position of hexose. In present work, synthesis of reversed C-glycopeptidomimetics (pseudoglycopeptides) was done by Passerini reaction protocol which is famous for peptide synthesis due to its mild conditions and easy workup. This paper discusses the use of α-D-galactose, a cheap and easily available monosaccharide to prepare reversed C-glycopeptidomimetics. The term reversed C-glycopeptidomimetics is derived for its analogy with reversed C-nucleosides, as in these reactions, instead of anomeric carbon i.e. more reactive site, C-6 undergoes to produce desired products.

A process for preparing N - aryl amide compound

The method discloses a method used for preparing an N-aryl amide compound from amides and aniline compounds. According to the method, a palladium salt and a ligand are taken as catalysts; an N,N-dimethyl formamide compound, an aniline compound, a protonic acid, a Lewis acid, and an organic solvent are mixed; and an obtained mixture is subjected to heating reaction so as to obtain the N-aryl amide compound. Advantages of the method are that: preparation route is short, substrate universality is excellent, reaction conditions are mild, synthesis yield is high, and used raw materials and catalysts are simple and easily available.

Formyloxyacetoxyphenylmethane as an N-Formylating Reagent for Amines, Amino Acids, and Peptides

Formyloxyacetoxyphenylmethane is a stable, water-tolerant, N-formylating reagent for primary and secondary amines that can be used under solvent-free conditions at room temperature to prepare a range of N-formamides, N-formylanilines, N-formyl-α-amino acids, N-formylpeptides, and an isocyanide.

An efficient reduction of N-substituted carbonylimidazolides into formamides by NaBH4

A novel, simple and versatile protocol was investigated for highly efficient synthesis of formamides through reducing N-substituted carbonylimidazolides by NaBH4 under mild reaction conditions. By this method, not only carboxylic acids or isocyanates, but also amines can readily access formamides with high yields.