52818-63-0

Usage

Uses

Used in Chemical Synthesis:
2-(4-Methoxybenzylamino)pyridine is used as a key intermediate in the synthesis of various organic compounds, particularly those involving the formation of Schiff bases. Its unique structure allows for further functionalization and the creation of novel molecules with potential applications in different industries.
Used in Microbiology Evaluations:
In the field of microbiology, 2-(4-Methoxybenzylamino)pyridine is utilized for evaluating the effectiveness of (N-heteroaryl)arylmethanamines and their Schiff bases. These evaluations are crucial for understanding the interactions between these compounds and microbial organisms, which can lead to the development of new antimicrobial agents or insights into their mechanisms of action.
Used in Pharmaceutical Research:
Given its structural features, 2-(4-Methoxybenzylamino)pyridine holds potential in the development of new pharmaceuticals. Its ability to form Schiff bases with various aldehydes and ketones can lead to the creation of new drug candidates with diverse biological activities, such as potential applications in the treatment of various diseases or conditions.
Used in Material Science:
2-(4-Methoxybenzylamino)pyridine's chemical properties, including its white to yellow powder form, may also find applications in material science. It could be used in the development of new materials with specific properties, such as those with unique optical, electronic, or mechanical characteristics.

InChI:InChI=1/C13H14N2O/c1-16-12-7-5-11(6-8-12)10-15-13-4-2-3-9-14-13/h2-9H,10H2,1H3,(H,14,15)/p+1

Upstream product

• 504-29-0 2-aminopyridine 
• 105-13-5 4-Methoxybenzyl alcohol 
• 824-94-2 p-methoxybenzyl chloride 
• 15009-91-3 2-nitropyridine 
• 2393-23-9 4-methoxy-benzylamine 
• 5029-67-4 2-iodopyridine 
• 123-11-5 4-methoxy-benzaldehyde 
• 40037-18-1 2-<(p-methoxybenzylidene)amino>pyridine 
• 462-08-8 pyridin-3-ylamine 
• 38427-94-0 N-(tert-butoxycarbonyl)-2-aminopyridine 
• 1445435-39-1 C₁₈H₂₂N₂O₃ 

Downstream Products

• 504-29-0 2-aminopyridine 
• 50-00-0 formaldehyd 
• 726-18-1 4,4'-dianisylmethane 
• 52818-55-0 4-Benzamido-1-(2-[N-(p-methoxybenzyl)-N-(2-pyridyl)]-amino)ethylpiperidine 
• 1009069-76-4 N-(4-methoxybenzyl)-N-(5-nitropyridin-2-yl)-N-(pyridin-2-yl)amine 
• 1345012-36-3 tert-butyl 4-(2-((4-methoxybenzyl)(pyridin-2-yl)amino)ethyl)piperazine-1-carboxylate 
• 1345012-43-2 (S)-tert-butyl 3-(2-((4-methoxybenzyl)(pyridin-2-yl)amino)acetamido)pyrrolidin-1-carboxylate 
• 1177415-99-4 6-chloro-N-(3-fluoropyridin-4-yl)-8-((4-methoxybenzyl)(pyridin-2-yl)amino)imidazo[1,2-b]pyridazine-3-carboxamide 

Relevant academic research and scientific papers

SYNTHESIS, STRUCTURE, AND PROPERTIES OF 1-(p-R-PHENACYL)-2-(p-METHOXYBENZYLAMINO)PYRIDINIUM BROMIDES

We have synthesized 2-(p-methoxybenzylamino)-1-(p-R-phenacyl)pyridinium bromides by alkylation of 2-(p-methoxybenzylamino)pyridine with substituted phenacyl bromides.Using spectral methods we have shown that the title compounds exist in the form of 1,2-diaryl-2-hydroxy-2,3-dihydroimidazopyridinium salts.We have studied their properties and suggest an alternative synthesis route.

ZnBr2 Mediated C?N Bond Formation using Cinnamyl Alcohol and 2-Amino Pyridines

A simple method for C?N bond formation is disclosed by using cinnamyl alcohols and 2-amino pyridine derivatives in the presence of stoichiometric amount of zinc bromide. This reaction works with a wide range of substrates, and is compatible with primary, secondary, and homoallylic alcohols. To the best of our knowledge, this is the first report for C?N bond formation using cinnamyl alcohol and 2-amino pyridines using zinc bromide as a Lewis acid.

[(PPh3)2NiCl2]-Catalyzed C-N bond formation reaction via borrowing hydrogen strategy: Access to diverse secondary amines and quinolines

Commercially available [(PPh3)2NiCl2] was found to be an efficient catalyst for the mono-N-alkylation of (hetero)- A romatic amines, employing alcohols to deliver diverse secondary amines, including the drug intermediates chloropyramine (5b) and mepyramine (5c), in excellent yields (up to 97%) via the borrowing hydrogen strategy. This method shows a superior activity (TON up to 10000) with a broad substrate scope at a low catalyst loading of 1 mol % and a short reaction time. Further, this strategy is also successful in accessing various quinoline derivatives following the acceptorless dehydrogenation pathway.

Ruthenium(ii) complexes with N-heterocyclic carbene-phosphine ligands for theN-alkylation of amines with alcohols

Metal hydride complexes are key intermediates forN-alkylation of amines with alcohols by the borrowing hydrogen/hydrogen autotransfer (BH/HA) strategy. Reactivity tuning of metal hydride complexes could adjust the dehydrogenation of alcohols and the hydrogenation of imines. Herein we report ruthenium(ii) complexes with hetero-bidentate N-heterocyclic carbene (NHC)-phosphine ligands, which realize smart pathway selection in theN-alkylated reactionviareactivity tuning of [Ru-H] species by hetero-bidentate ligands. In particular, complex6cbwith a phenyl wingtip group and BArF?counter anion, is shown to be one of the most efficient pre-catalysts for this transformation (temperature is as low as 70 °C, neat conditions and catalyst loading is as low as 0.25 mol%). A large variety of (hetero)aromatic amines and primary alcohols were efficiently converted into mono-N-alkylated amines in good to excellent isolated yields. Notably, aliphatic amines, challenging methanol and diamines could also be transformed into the desired products. Detailed control experiments and density functional theory (DFT) calculations provide insights to understand the mechanism and the smart pathway selectionvia[Ru-H] species in this process.

Convenient and Reusable Manganese-Based Nanocatalyst for Amination of Alcohols

The development of new sustainable nanocatalytic systems for green chemical synthesis is a growing area in chemical science. Herein, a reusable heterogeneous N-doped graphene-based manganese nanocatalyst (Mn@NrGO) for selective N-alkylation of amines with alcohols is described. Mechanistic studies illustrate that the catalytic reaction follows a domino dehydrogenation-condensation-hydrogenation sequence of alcohols and amines with the formation of water as the sole by-product. The scope of the reaction is extended to the synthesis of pharmaceutically important N-alkylated amine intermediates. The heterogeneous nature of the catalyst made it easy to separate for long-term performance, and the recycling study revealed that the catalyst was robust and retained its activity after several recycling experiments.

Water-promoted dehydrative coupling of 2-aminopyridines in heptane: Via a borrowing hydrogen strategy

A synthetic method for dehydrative N-benzylation promoted by water molecules in heptane using a π-benzylpalladium system has been developed. The presence of water significantly accelerates carbon-nitrogen bond formation, which is accomplished in an atom-economical process to afford the corresponding N-monobenzylated products. A crossover experiment afforded H/D scrambled products, which is consistent with a borrowing hydrogen mechanism. Kinetic isotope effect measurements revealed that benzylic carbon-hydrogen bond cleavage was the rate-determining step.

Designed pincer ligand supported Co(ii)-based catalysts for dehydrogenative activation of alcohols: Studies onN-alkylation of amines, α-alkylation of ketones and synthesis of quinolines

Base-metal catalystsCo1,Co2andCo3were synthesized from designed pincer ligandsL1,L2andL3having NNN donor atoms respectively.Co1,Co2andCo3were characterized by IR, UV-Vis. and ESI-MS spectroscopic studies. Single crystal X-ray diffraction studies were investigated to authenticate the molecular structures ofCo1andCo3. CatalystsCo1,Co2andCo3were utilized to study the dehydrogenative activation of alcohols forN-alkylation of amines, α-alkylation of ketones and synthesis of quinolines. Under optimized reaction conditions, a broad range of substrates including alcohols, anilines and ketones were exploited. A series of control experiments forN-alkylation of amines, α-alkylation of ketones and synthesis of quinolines were examined to understand the reaction pathway. ESI-MS spectral studies were investigated to characterize cobalt-alkoxide and cobalt-hydride intermediates. Reduction of styrene by evolved hydrogen gas during the reaction was investigated to authenticate the dehydrogenative nature of the catalysts. Probable reaction pathways were proposed forN-alkylation of amines, α-alkylation of ketones and synthesis of quinolines on the basis of control experiments and detection of reaction intermediates.

N-Alkylation of Amines with Alcohols Catalyzed by Manganese(II) Chloride or Bromopentacarbonylmanganese(I)

A manganese-catalyzed N-alkylation reaction of amines with alcohols via hydrogen autotransfer strategy has been demonstrated. The developed practical catalytic system including an inexpensive, nontoxic, commercially available MnCl2 or MnBr(CO)5 as the metal salt and triphenylphosphine as a ligand provides access to diverse aromatic, heteroaromatic, and aliphatic secondary amines in moderate-to-high yields. In addition, this operationally simple protocol is scalable to the gram level and suitable for synthesizing heterocycles such as indole and resveratrol-derived amines known to be active for Alzheimer's disease.

Ru(II)-NHC catalysed N-Alkylation of amines with alcohols under solvent-free conditions

The reaction of [RuCl2(p-cymene)]2 with in situ prepared Ag-N-heterocyclic carbene (NHC) complexes yields a series of [RuCl2(p-cymene)(NHC)] complexes (2). All of the complexes have been characterised by elemental analysis, and 1H NMR and 13C NMR spectroscopies. These complexes have been tested for the N-alkylation of aromatic amines with arylmethyl alcohols under neat conditions in the presence of KOtBu at 120 °C. Compounds (2) are stable and have high catalytic/selective activity for the N-alkylation reactions of primary amines to afford secondary amines.

Half-sandwich Ru(ii) arene complexes bearing benzimidazole ligands for theN-alkylation reaction of aniline with alcohols in a solvent-free medium

In this article, the directN-alkylation reactions of amines with alcohol derivatives using the borrowing hydrogen methodology have been investigated. For this purpose, a new series of half-sandwich ruthenium(ii) complexes bearing N-coordinated benzimidazole complexes have been synthesized and fully characterized by FT-IR,1H NMR and13C NMR spectroscopies. Additionally, the structures of the complexes2a-2ehave been characterized by X-ray crystallography. All new complexes were investigated for their catalytic activities in the alkylation reaction of amines with alcohol derivatives. It was found that alkylation reactions in a solvent-free medium are efficient and selective.