Category: 52818-63-0

Reddy, P. Srinivasa published the artcileReductive amination of carbonyl compounds using NaBH₄ in a Bronsted acidic ionic liquid, COA of Formula: C13H14N2O, the publication is Tetrahedron Letters (2007), 48(50), 8807-8810, database is CAplus.

Reductive amination of carbonyl compounds using sodium borohydride is conducted in the Bronsted acidic ionic liquid, 1-methylimidazolium tetrafluoroborate ([HMIm][BF₄]). The ionic liquid plays the dual role of solvent as well as catalyst for efficient conversion of aldehydes and ketones to amines in excellent yields without the formation of side products.

Tetrahedron Letters published new progress about 52818-63-0. 52818-63-0 belongs to ethers-buliding-blocks, auxiliary class Pyridine,Amine,Benzene,Ether, name is N-(4-Methoxybenzyl)pyridin-2-amine, and the molecular formula is C13H14N2O, COA of Formula: C13H14N2O.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Sun, Jian published the artcileNi-Cu/γ-Al₂O₃ catalyzed N-alkylation of amines with alcohols, Safety of N-(4-Methoxybenzyl)pyridin-2-amine, the publication is Catalysis Communications (2012), 30-33, database is CAplus.

A γ-Al₂O₃-supported Ni and Cu bimetallic nanoparticles catalyst (45 weight % Ni, Ni/Cu mass ratio = 4.5/1.0) is prepared by electroless plating method for the N-alkylation of amines with alcs. under base and Lewis acidic cocatalyst conditions. The catalyst afforded fast conversions, high selectivity for amines and alcs. with various structures under an argon atm. in o-xylene. Furthermore, the catalyst still has a stable catalytic activity after being regenerated for two consecutive cycles.

Catalysis Communications published new progress about 52818-63-0. 52818-63-0 belongs to ethers-buliding-blocks, auxiliary class Pyridine,Amine,Benzene,Ether, name is N-(4-Methoxybenzyl)pyridin-2-amine, and the molecular formula is C6H3F2NO3, Safety of N-(4-Methoxybenzyl)pyridin-2-amine.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Yu, Xiaochun published the artcilePalladium-Catalyzed N-Alkylation of Amides and Amines with Alcohols Employing the Aerobic Relay Race Methodology, Recommanded Product: N-(4-Methoxybenzyl)pyridin-2-amine, the publication is Chinese Journal of Chemistry (2012), 30(10), 2322-2332, database is CAplus.

Possibly because homogeneous palladium catalysts are not typically borrowing hydrogen catalysts and ligands are thus ineffective in catalyst activation under conventional anaerobic conditions, they had not been used in the N-alkylation reactions of amines/amides with alcs. in the past. By employing the aerobic relay race method with Pd-catalyzed aerobic alc. oxidation being a more effective protocol for alc. activation, ligand-free homogeneous palladium are successfully used as active catalysts in the dehydration N-alkylation reactions, giving high yields and selectivities of the alkylated amides and amines. Mechanistic studies implied that the reaction most probably proceeds by a novel relay race mechanism that was recently discovered and proposed.

Chinese Journal of Chemistry published new progress about 52818-63-0. 52818-63-0 belongs to ethers-buliding-blocks, auxiliary class Pyridine,Amine,Benzene,Ether, name is N-(4-Methoxybenzyl)pyridin-2-amine, and the molecular formula is C9H6BrNO, Recommanded Product: N-(4-Methoxybenzyl)pyridin-2-amine.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Hikawa, Hidemasa published the artcileA borrowing hydrogen methodology: palladium-catalyzed dehydrative N-benzylation of 2-aminopyridines in water, Formula: C13H14N2O, the publication is Green Chemistry (2018), 20(13), 3044-3049, database is CAplus.

A greener borrowing hydrogen methodol. using the π-benzylpalladium system, which offered an efficient and environmentally friendly preparation of N-benzyl aminopyridines I [R¹ = H, 5-F, 3-Me, etc.; R² = H, 3-Me, 4-t-BuO, etc.; R³ = H, Me] via dehydrative N-monobenzylation of 2-aminopyridines with benzylic alcs. in the absence of base was demonstrated. The crossover experiment using benzyl-α,α-d₂ alc. and 3-methylbenzyl alc. afforded H/D scrambled products, suggesting that the dehydrative N-benzylation in the catalytic system involved a borrowing hydrogen pathway. KIE experiments showed that C-H bond cleavage at the benzylic position of benzyl alc. was involved in the rate-determining step (KIE = 2.9). This simple base-free protocol could be achieved under mild conditions in an atom-economic process, affording the desired products in moderate to excellent yields.

Green Chemistry published new progress about 52818-63-0. 52818-63-0 belongs to ethers-buliding-blocks, auxiliary class Pyridine,Amine,Benzene,Ether, name is N-(4-Methoxybenzyl)pyridin-2-amine, and the molecular formula is C13H14N2O, Formula: C13H14N2O.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Feng, Xinshu published the artcileEffect of the ancillary ligand in N-heterocyclic carbene iridium(III) catalyzed N-alkylation of amines with alcohols, SDS of cas: 52818-63-0, the publication is Polyhedron (2021), 115289, database is CAplus.

A series of air-stable N-heterocyclic carbene (NHC) Ir(III) complexes (Ir1-Ir6), bearing various combinations of chlorine, pyridine and NHC ligands, were assayed for the N-alkylation of amines with alcs. It was found that Ir3, with two monodentate 1,3-bis-methyl-imidazolylidene (IMe) ligands, emerged as the most active complex. A large variety of amines and primary alcs. were efficiently converted into mono-N-alkylated amines in 53-96% yields. As a special highlight, for the challenging MeOH, selective N-monomethylation could be achieved using KOH as a base under an air atm. Moreover, this catalytic system was successfully applied to the gram-scale synthesis of some valuable compounds

Polyhedron published new progress about 52818-63-0. 52818-63-0 belongs to ethers-buliding-blocks, auxiliary class Pyridine,Amine,Benzene,Ether, name is N-(4-Methoxybenzyl)pyridin-2-amine, and the molecular formula is C13H14N2O, SDS of cas: 52818-63-0.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Nakayama, Taku published the artcileWater-promoted dehydrative coupling of 2-aminopyridines in heptane via a borrowing hydrogen strategy, COA of Formula: C13H14N2O, the publication is RSC Advances (2021), 11(37), 23144-23150, database is CAplus and MEDLINE.

A synthetic method for dehydrative N-benzylation promoted by water mols. 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.

RSC Advances published new progress about 52818-63-0. 52818-63-0 belongs to ethers-buliding-blocks, auxiliary class Pyridine,Amine,Benzene,Ether, name is N-(4-Methoxybenzyl)pyridin-2-amine, and the molecular formula is C13H14N2O, COA of Formula: C13H14N2O.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Liang, Dongdong published the artcileA Metal-Free Tandem Demethylenation/C(sp²)-H Cycloamination Process of N-Benzyl-2-aminopyridines via C-C and C-N Bond Cleavage, Product Details of C13H14N2O, the publication is Organic Letters (2013), 15(13), 3476-3479, database is CAplus and MEDLINE.

A mild, metal-free synthesis of pyrido[1,2-a]benzimidazoles starting with N-benzyl-2-aminopyridines, which employs PhI(OPiv)₂ as a stoichiometric oxidant, has been developed. The process is initiated by an unusual PhI(OPiv)₂-mediated ipso S_EAr reaction, followed by solvent-assisted C-C and C-N bond cleavage.

Organic Letters published new progress about 52818-63-0. 52818-63-0 belongs to ethers-buliding-blocks, auxiliary class Pyridine,Amine,Benzene,Ether, name is N-(4-Methoxybenzyl)pyridin-2-amine, and the molecular formula is C13H14N2O, Product Details of C13H14N2O.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Hirao, Ichiro published the artcileCondensation of anisyl alcohol or benzyl alcohol with aromatic amines, Synthetic Route of 52818-63-0, the publication is Yakugaku Zasshi (1954), 853-5, database is CAplus.

A mixture of 7 g. p-MeOC₆H₄CH₂OH (I), 5 g. 2-aminopyridine (II), 20 g. xylene, and 4 g. KOH refluxed 21 hrs., extracted with 10% HCl, KOH added to pH 7, and the product recrystallized from dilute MeOH give 8.9 g. (80%) 2-(p-methoxybenzylamino)pyridine (III), m. 108°, or 5.5 g. I, 3.5 g. II, 8 g. PhMe, and 4 g. KOH refluxed 12 hrs. and the product treated as above give 4.8 g. (62%) III, m. 123-4°. I (7 g.), 4.7 g. PhNH₂, 20 g. xylene, and 4 g. KOH refluxed 21 hrs., and the product precipitated with 10% HCl, dissolved in KOH, and recrystallized from MeOH gives 5 g. (51%) p-MeOC₆H₄CH₂NHPh, m. 63-4°. Similarly, 20 g. PhCH₂OH, 6 g. 2-aminopyrimidine, 40 g. PhMe, and 7 g. KOH refluxed 10 hrs. give 16 g. (44%) 2-benzylaminopyrimidine, m. 79-81°; 8 g. PhCH₂OH, 6 g. 2-H₂NC₅H₄N, 4 g. PhMe, and 15 g. PhMe refluxed 13 hrs. give 11 g. (81%) 2-PhCH₂NHC₅H₄N, m. 95-6°; 10.8 g. PhCH₂OH, 9.3 g. PhNH₂, 40 g. xylene, and 8 g. KOH refluxed 21 hrs. give 1.47 g. PhCH₂NHPh.HCl, m. 214-5°.

Yakugaku Zasshi published new progress about 52818-63-0. 52818-63-0 belongs to ethers-buliding-blocks, auxiliary class Pyridine,Amine,Benzene,Ether, name is N-(4-Methoxybenzyl)pyridin-2-amine, and the molecular formula is C13H14N2O, Synthetic Route of 52818-63-0.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Cicek, Metin published the artcileHalf-sandwich Ru(II) arene complexes bearing benzimidazole ligands for the N-alkylation reaction of aniline with alcohols in a solvent-free medium, Quality Control of 52818-63-0, the publication is New Journal of Chemistry (2021), 45(25), 11075-11085, database is CAplus.

The direct N-alkylation reactions of amines with alc. derivatives using the borrowing hydrogen methodol. were investigated. For this purpose, a new series of half-sandwich ruthenium(II) complexes bearing N-coordinated benzimidazole complexes were synthesized and fully characterized by FT-IR, ¹H NMR and ¹³C NMR spectroscopies. Addnl., the structures of the complexes were characterized by X-ray crystallog. All new complexes were investigated for their catalytic activities in the alkylation of amines with alc. derivatives It was found that alkylation reactions in a solvent-free medium were efficient and selective.

New Journal of Chemistry published new progress about 52818-63-0. 52818-63-0 belongs to ethers-buliding-blocks, auxiliary class Pyridine,Amine,Benzene,Ether, name is N-(4-Methoxybenzyl)pyridin-2-amine, and the molecular formula is C13H14N2O, Quality Control of 52818-63-0.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem

Furst, Hans published the artcileAlkylamino pyridines and alkyl pyridine ethers. (Relations between chemical constitution and odor.), Category: ethers-buliding-blocks, the publication is Chemische Technik (Leipzig, Germany) (1958), 693-9, database is CAplus.

The synthesis of alkylandnopyridines and alkyl pyridine ethers was reported. In all cases below are given in parentheses, n²⁰_D, b.p./mm., and odor, if any, resp. 2-(Substituted amino)-pyridines were prepared by the method of Sharp (C.A. 34, 1663⁸) in 30-70% yield (substituents given: iso-Bu (1.5328, 69°/2, mignonette); n-hexyl (-,111°/2, strong mignonette); phenylethyl (-, 158°/3, weak mignonette); Et, Bu (1.5251, 125°/2, strong salicylic, ester); ethyl, n-decyl (1.5085, 132°/2, weak); ethyl, benzyl (1.5947, 112°/2, weak mignonette). 2-Methyl-6-(substituted amino)pyridine derivatives were prepared from 2-methyl-6-aminopyridine by the Tschitschibabin procedure in 80% yields: Bu (1.5329, 82°/2, earthy); iso-Am (1.5170, 91°/2, penetrating); n-hexyl (1.5205, 108°/2, weak mignonette); Et, Bu (1.5195, 85°/1, earthy); n-Pr, Bu (1.5153, 90°/1, weak mignonette); n-hexyl, Bu (1.5063, 112°/1, weak earthy). Also prepared were 2,6-Pr(PrBuN)C₅H₃N (1.5142, 90°/1, burnt), and 2,6-Bu(PrBuN)C₅H₃N (1.5138, 104°/1, burnt). 3-Methyl-6-(substituted amino)pyridine derivatives, in about 80% yields, were prepared according to the method of Stuart: Bu (1.5351, 74°/2, mignonette); n-hexyl (1.5250, 98/2, woody); benzyl (-, 122°/2, earthy, m. 76°); Et, Bu (1.5129, 72°/1, weak mignonette). 4-Methyl-6-(substituted amino)pyridine derivatives were prepared from 4-methyl-6-aminopyridine: Bu(-, 82°/2, flowery, m. 41°); iso-Bu (1.5348, 75°7/2, rooty); benzyl (-, -, weak mignonette, m. 76°); Et, Bu (1.5197, 82°/1, weak mignonette). 2-Pyridyl alkyl ethers were prepared from 2-bromopyridine and the alcs. in 60% yields (alkyl given): n-hexyl (1.4878, 73°/2, fruity); n-heptyl (1.4850, 83°/2, pleasant); isoöctyl (1.4825, 85°/2, fruity); cyclohexyl (1.5242, 65°/2, -). 2-Alkyl-6-pyridyl alkyl ethers were prepared from the corresponding ethers, NaNH₂, and the alkyl halides in 70% yields: 2-(n-butyl)-6-pyridyl, n-hexyl (1.5186, 72°/0.5, burnt); 2-(n-amyl)-6-pyridyl, n-heptyl (1.5123, 85°/0.5, celery); 2-isohexyl-6-pyridyl, n-amyl (1.4900, 98°/0.5, weak elder); 2-(n-nonyl)-6-pyridyl, n-amyl (1.4859, 130°/0.5, weak elder). 2-Methyl-6-(R-substituted)pyridine derivatives (R = alkyl or aryl) were prepared from 2,6-dimethylpyridine and R halide plus NaNH₂: Am (1.4869, 69°/2, rooty); n-hexyl (1.4867, 79°/2, rooty); n-heptyl (1.4854, 89/2, pea-like); cyclohexyl (1.5185, 75°/2, fatty); benzyl (1.5644, 94°/2, fruity). 2-Methyl-6-alkyl-pyridines were also prepared as above: isohexyl (1.4858, 52°/2, rooty), n-heptyl (1.4820, 65°/2, pealike); n-nonyl (1.4826, 85°/2, fatty); and phenylethyl (1.5679, 91°/2, fruity and leafy).

Chemische Technik (Leipzig, Germany) published new progress about 52818-63-0. 52818-63-0 belongs to ethers-buliding-blocks, auxiliary class Pyridine,Amine,Benzene,Ether, name is N-(4-Methoxybenzyl)pyridin-2-amine, and the molecular formula is C13H14N2O, Category: ethers-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem