19614-15-4

Usage

Uses

Used in Pharmaceutical Industry:
ETHYL 4-MORPHOLINOBENZENECARBOXYLATE is used as an intermediate in the synthesis of various pharmaceutical products due to its unique structural features, including a morpholine ring and a carboxylic acid group, which contribute to the development of new drugs.
Used in Organic Synthesis:
In the realm of organic chemistry, ETHYL 4-MORPHOLINOBENZENECARBOXYLATE is utilized as a reagent, playing a crucial role in various chemical reactions and contributing to the synthesis of a wide range of organic compounds.
Used in Agricultural Chemical Production:
ETHYL 4-MORPHOLINOBENZENECARBOXYLATE also serves as a precursor in the production of agricultural chemicals, where its chemical properties are harnessed to create substances that aid in crop protection and enhancement of agricultural yields.

InChI:InChI=1/C13H17NO3/c1-2-17-13(15)11-3-5-12(6-4-11)14-7-9-16-10-8-14/h3-6H,2,7-10H2,1H3

Upstream product

• 111-44-4 3-oxa-1,5-dichloropentane 
• 94-09-7 p-aminoethylbenzoate 
• 110-91-8 morpholine 
• 51934-41-9 4-iodobenzoic acid ethyl ester 
• 5765-65-1 4-(benzoyloxy)morpholine 
• 7335-27-5 ethyl 4-chlorobenzoate 
• 17159-79-4 ethyl 4-oxocyclohexane-1-carboxylate 
• 34604-52-9 diethylene glycol dimesylate 
• 1312161-41-3 C₂₇H₂₇O₁₀P 
• 5798-75-4 Ethyl 4-bromobenzoate 
• 451-46-7 4-fluorobenzoic acid ethyl ester 

Downstream Products

• 19620-58-7 bis-(2-methylsulfanylmethyl-phenyl)-(4-morpholin-4-yl-phenyl)-methanol 
• 7470-38-4 4-morpholin-4-yl-benzoic acid 
• 183557-77-9 (4-morpholin-4-yl-phenyl)-amide 
• 720720-60-5 4-(3-oxomorpholin-4-yl)benzoic acid 
• 766556-56-3 ethyl 4-(3-oxomorpholino)benzoate 

Relevant academic research and scientific papers

Electrochemical Cross-Dehydrogenative Aromatization Protocol for the Synthesis of Aromatic Amines

The introduction of amines onto aromatics without metal catalysts and chemical oxidants is synthetically challenging. Herein, we report the first example of an electrochemical cross-dehydrogenative aromatization (ECDA) reaction of saturated cyclohexanones and amines to construct anilines without additional metal catalysts and chemical oxidants. This reaction exhibits a broad scope of cyclohexanones including heterocyclic ketones, affording a variety of aromatic amines with various functionalities, and shows great potential in the synthesis of biologically active compounds.

Amination of Aryl Halides Mediated by Electrogenerated Nickel from Sacrificial Anode

Electrochemical C(sp2)?N couplings mediated by nickel salts generated from the sacrificial anode has been described for the first time. In this approach, the sacrificial nickel anode is employed as the sole source of nickel and the process, operationally simple to set up, enables the preparation of functionalized arylamine derivatives with moderate to good yields, under mild reaction conditions and without additional ligand. A cooperative process between the two electrodes is involved in the proposed mechanism.

Dihalogen-bridged NHC-palladium(i) dimers: Synthesis, characterisation and applications in cross-coupling reactions

A di-iodo-bridged PdI dimer bearing an N-heterocyclic carbene ligand was made accessible via the reduction of [(IPr)PdI2]2 in basic methanol solution. The structural features of [(IPr)PdI]2 were explored by single-crystal X-ray analysis. It was found to be a convenient one-component precatalyst with high activity in Suzuki-Miyaura, Buchwald-Hartwig, and Sonogashira reactions.

Organic semiconductor photocatalyst can bifunctionalize arenes and heteroarenes

Photoexcited electron-hole pairs on a semiconductor surface can engage in redox reactions with two different substrates. Similar to conventional electrosynthesis, the primary redox intermediates afford only separate oxidized and reduced products or, more rarely, combine to one addition product. Here, we report that a stable organic semiconductor material, mesoporous graphitic carbon nitride (mpg-CN), can act as a visible-light photoredox catalyst to orchestrate oxidative and reductive interfacial electron transfers to two different substrates in a two- or three-component system for direct twofold carbon–hydrogen functionalization of arenes and heteroarenes. The mpg-CN catalyst tolerates reactive radicals and strong nucleophiles, is straightforwardly recoverable by simple centrifugation of reaction mixtures, and is reusable for at least four catalytic transformations with conserved activity.

Silver-catalyzed intermolecular amination of fluoroarenes

A novel highly selective Ag-catalyzed intermolecular amination of fluoroarenes has been developed. This transformation starts from readily available 4-carbonyl fluorobenzene and NaN3 or other nitrogen-source, via amination followed by C-F bond cleavage, thus affording the desired 4-carbonyl arylamine products under mild conditions. The reaction is accelerated using a small amount of water. This pathway is distinct from a previously reported radical amination reaction.

Design, synthesis and biological evaluation of a series of novel 2-benzamide-4-(6-oxy-N-methyl-1-naphthamide)-pyridine derivatives as potent fibroblast growth factor receptor (FGFR) inhibitors

Starting from the phase II clinical FGFR inhibitor lucitanib (2), we conducted a medicinal chemistry approach by opening the central quinoline skeleton coupled with a scaffold hopping process thus leading to a series of novel 2-benzamide-4-(6-oxy-N-methyl-1-naphthamide)-pyridine derivatives. Compound 25a was identified to show selective and equally high potency against FGFR1/2 and VEGFR2 with IC50 values less than 5.0 nM. Significant antiproliferative effects on both FGFR1/2 and VEGFR2 aberrant cancer cells were observed. In the SNU-16 xenograft model, compound 25a showed tumor growth inhibition rates of 25.0% and 81.0% at doses of 10 mg/kg and 50 mg/kg, respectively, with 5% and 10%body weight loss. In view of the synergistic potential of FGFs and VEGFs in tumor angiogenesis observed in preclinical studies, the FGFR/VEGFR2 dual inhibitor 25a may achieve better clinical benefits.

Pyrazolo [3,4 - the b] pyridine and [...] composition preparation method and use of (by machine translation)

The present invention provides a pyrazolo [3,4 - the b] pyridine and [...] compound of preparation and use, in particular, the present invention provides a following formula (I) compounds are shown, wherein the definition of each group as described in the specification. The compounds of the invention has excellent tyrosine kinase inhibiting activity, so can be used for preparing a series of treating diseases associated with the tyrosine kinase activity of the drug. (by machine translation)

Rapid and convenient synthesis of N-arylmorpholines under microwave irradiation

A series of N-arylmorpholines 1a-1n was obtained by cyclocondensation of arylamines and diethylene glycol dimesylate under microwave irradiation in an aqueous potassium carbonate medium. The reaction is rapid and convenient, and a variety of functional groups are tolerated in the process.

Nickel-catalyzed amination of aryl phosphates through cleaving aryl C-O bonds

The amination of triaryl phosphates was achieved using a Ni(II)-(σ-Aryl) complex/NHC catalyst system in dioxane at 110 °C in the presence of NaH as base. Electron-neutral, -rich, and -deficient triaryl phosphates were coupled with a wider range of amine partners including cyclic and acyclic secondary amines, aliphatic primary amines, and anilines in good to excellent yields.

Evaluation of aromatic amination catalyzed by palladium on carbon: A practical synthesis of triarylamines

A heterogeneous palladium on carbon (Pd/C)-catalyzed coupling between amines and aromatic halides including aromatic chlorides has been achieved using sodium tert-butoxide (NaO-t-Bu) and 1,1′-bis(diphenylphosphino)ferrocene (dppf) as a ligand in cyclopentyl methyl ether (CPME). The use of potassium tert-butoxide (KO-t-Bu) in place of NaO-t-Bu brought about the benzyne-mediated aromatic amination even without Pd/C and dppf, giving a mixture of regioisomers when 4-substituted bromobenzenes were employed as the substrate. The combination of Pd/C, dppf, NaO-t-Bu could be utilized for the syntheses of a broad range of triarylamines by replacing CPME with mesitylene which can provide a higher reaction temperature. The Pd/C could be quantitatively recovered and reused until at least the fourth cycle without any loss in catalytic activity. The quite low leaching of palladium (1.1%) was demonstrated by an inductively coupled plasma-atomic emission spectrometric analysis.