73938-86-0

Upstream product

• 108-42-9 3-chloro-aniline 
• 504-63-2 trimethyleneglycol 
• 74-85-1 ethene 
• 932-96-7 N-methyl(p-chloroaniline) 
• 17745-45-8 propylboronic acid 
• 106-47-8 4-chloro-aniline 
• 780-21-2 N-(4-chlorobenzylidene)aniline 
• 2759-54-8 N-(4-chlorophenyl)propionamide 
• 71-43-2 benzene 
• 123-38-6 propionaldehyde 

Downstream Products

• 55239-36-6 C₁₀H₁₁Cl₂NO 
• 55246-81-6 C₁₀H₁₁Cl₂NS 
• 642410-38-6 2-bromo-N-(4-chlorophenyl)-N-propylacetamide 

Relevant academic research and scientific papers

Titanium-Catalyzed Hydroaminoalkylation of Ethylene

The first examples of titanium-catalyzed hydroaminoalkylation reactions of ethylene with secondary amines are presented. The reactions can be achieved with various titanium catalysts and they do not require the use of high pressure equipment. In addition, the first solid-state structure of a titanapyrrolidine that is formed by insertion of an alkene into the Ti?C bond of a titanaaziridine is reported.

Catalytic Synthesis of Substituted Indoles and Quinolines from the Dehydrative C-H Coupling of Arylamines with 1,2- and 1,3-Diols

The cationic ruthenium-hydride complex catalyzes the dehydrative C-H coupling reaction of arylamines with 1,2-diols to form the indole products. The analogous coupling of arylamines with 1,3-diols afforded the substituted quinolines. The catalytic method directly forms these coupling products in a highly regioselective manner without generating any toxic byproducts.

Selective copper-promoted cross-coupling of aromatic amines with alkyl boronic acids

A simple copper-promoted N-monoalkylation of anilines that utilizes alkyl boronic acids as the alkylating partner is presented. The reaction is carried out in refluxing dioxane, and it allows a number of structurally and electronically diverse anilines to be functionalized in a single step. A broad study was carried out to demonstrate the utility of this new methodology for the preparation of phenethylanilines.

HETEROCYCLIC DERIVATIVE HAVING INHIBITORY ACTIVITY ON TYPE-I 11 -HYDROXYSTEROID DEHYDROGENASE

Disclosed is a compound which is useful as an 11β-hydroxysteroid dehydrogenase type 1 inhibitor. A compound represented by the formula: its pharmaceutically acceptable salt, or a solvate thereof, wherein X is O or S, a broken line and a wavy line represent the presence or the absence of a bond, (i) when a broken line represents the presence of a bond, a wavy line represents the absence of a bond, R2 and R3 are each independently hydrogen, halogen, cyano, hydroxy, carboxy, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl or the like, (ii) when a broken line represents the absence of a bond, a wavy line represents the presence of a bond, R1 and R4 are each independently hydrogen, halogen or the like, R2 and R3 are each independently hydrogen, halogen, cyano, hydroxy, carboxy, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl or the like, and R5 and R6 are each independently hydrogen, optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl or the like.

Solid phase approaches to N-heterocycles using a sulfur linker cleaved by SmI2

A sulfur HASC (α-hetero-atom substituted carbonyl) linker has been utilized in solid-phase approaches to oxindoles and tetrahydroquinolones. The route to oxindoles employs the first Pummerer cyclizations on solid phase, whereas the route to tetrahydroquinolones involves a microwave-assisted Heck reaction followed by a Michael cyclization. In both cases, the linker is cleaved in a traceless fashion by electron transfer from samarium(II) iodide. The routes illustrate the compatibility of the linker system with a number of reaction types and its utility for library synthesis.

High-pressure alkylation of azomethines 1. Synthesis of N-monoalkylanilines

Reaction of anils with alkyl halides under high pressure (10 kbar) was studied. Alkylation in polar media (dioxane or acetonitrile) followed by hydrolysis yields pure N-monoalkylanilines in high yields. Optimum conditions for high-pressure alkylation were found.

Sodium Borohydride Reduction of Adducts of Primary Amines with Aldehydes and p-Thiocresol. The Alkylation of Heterocyclic and Aromatic Amino-compounds

p-Nitroaniline, 2-aminopyridine (1a), 4-aminopyridine (2a), 2-amino-4-methylpyrimidine (8a), 2-aminothiazole (10a), and 2-aminobenzimidazole (12a) react with aqueous formaldehyde and p-thiocresol in ethanol or methanol solution to give N-(p-tolylthiomethyl) derivatives , usually in high yields.When the latter compounds are heated, under reflux, with an excess of sodium borohydride in ethanol or 1,2-dimethoxyethane solution, the corresponding methylamino-compounds are obtained.By a similar two-step prosedure in which aqueous formaldehyde is replaced, as appropriate, by anhydrous acetaldehyde, propionaldehyde, or benzaldehyde, p-nitroaniline is converted into N-ethyl-p-nitroaniline, p-chloroaniline is converted into p-chloro-N-(n-propyl)aniline, (1a) is converted into the corresponding ethylamino- and benzylamino-compounds (1c) and (1d), respectively, and (10a) and (12a) are converted into their 2-N-(n-propyl) derivatives (10c) and (12c), respectively.

Synthese de N-Alkyl-arylamines par Thermolyse ou Photolyse d'Alkyl-3-diaryl-1,3-triazenes

The thermolysis of 3-alkyl-1,3-bis(p-chlorophenyl)triazenes in benzene or methanol leads to the formation of N-alkyl-p-chloroanilines (2) in 19-50 percent yield, N-alkyl-bis(p-chlorophenyl)amines (3) in 7.5-15.5 percent yield and 4,4'-dichlorobiphenyle (4) in 1-7 percent yield; besides with benzene as the substrate, 4-chlorobiphenyle (5) (12-20 percent yield) was also formed.The photolysis in methanol gives only the N-alkyl-p-chloroanilines (2) in 32-40 percent yield.In these two cases the results are consistent with a radical pair formation in a solvent cage, recombination (thermolysis) and/or diffusion (thermolysis and photolysis) with intermolecular abstraction of hydrogen.A free radical chain mechanism is involved in the photolytic process and the quantum yield is high.