Category: 52818-63-0

Yu, Xiaochun published the artcileManganese Dioxide Catalyzed N-Alkylation of Sulfonamides and Amines with Alcohols under Air, Quality Control of 52818-63-0, the publication is Organic Letters (2011), 13(23), 6184-6187, database is CAplus and MEDLINE.

By simply running the reactions under air and solvent-free conditions using catalytic amounts of manganese dioxide, a practical and efficient N-alkylation method for a variety of sulfonamides and amines using alcs. as green alkylating reagents was developed.

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 C4H6O3, Quality Control of 52818-63-0.

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

Liu, Chuanzhi published the artcileDiscovery and Mechanistic Studies of a General Air-Promoted Metal-Catalyzed Aerobic N-Alkylation Reaction of Amides and Amines with Alcohols, Product Details of C13H14N2O, the publication is Journal of Organic Chemistry (2011), 76(14), 5759-5773, database is CAplus and MEDLINE.

The thermodynamically unfavorable anaerobic dehydrogenative alc. activation to aldehydes and hydridometal species is the bottleneck in metal-catalyzed N-alkylations due to a general and unnoticed catalyst deactivation by amines/amides. Thus, different from the anaerobic dehydrogenation process in borrowing hydrogen or hydrogen autotransfer reactions that require noble metal complexes or addition of capricious ligands for catalyst activation, the water-producing, exothermic, metal-catalyzed aerobic alc. oxidation is thermodynamically more favorable and the most effective and advantageous aldehyde generation protocol. This leads to a general and advantageous air-promoted metal-catalyzed aerobic N-alkylation methodol. that effectively uses many simpler, less expensive, more available, and ligand-free metal catalysts that were inactive under typical anaerobic borrowing hydrogen conditions, avoiding the use of preformed metal complexes and activating ligands and the exclusive requirement of inert atm. protection. This aerobic method is quite general in substrate scope and tolerates various amides, amines, and alcs., revealing its potentially broad utilities and interests in academy and industry. In contrast to the commonly accepted borrowing hydrogen mechanism, based on a thorough mechanistic study and supported by the related literature background, a new mechanism analogous to the relay race game that has never been proposed in metal-catalyzed N-alkylation reactions is presented.

Journal of Organic 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, Product Details of C13H14N2O.

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

Huang, Ming published the artcileRuthenium(II) complexes with N-heterocyclic carbene-phosphine ligands for the N-alkylation of amines with alcohols, Related Products of ethers-buliding-blocks, the publication is Organic & Biomolecular Chemistry (2021), 19(15), 3451-3461, database is CAplus and MEDLINE.

Metal hydride complexes are key intermediates for N-alkylation of amines with alcs. by the borrowing hydrogen/hydrogen autotransfer (BH/HA) strategy. Reactivity tuning of metal hydride complexes could adjust the dehydrogenation of alcs. 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 the N-alkylated reaction via reactivity tuning of [Ru-H] species by hetero-bidentate ligands. In particular, complex I·BArF^– with a Ph 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 alcs. 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 d. functional theory (DFT) calculations provide insights to understand the mechanism and the smart pathway selection via [Ru-H] species in this process.

Organic & Biomolecular 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, Related Products of ethers-buliding-blocks.

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

Li, Xiaohui published the artcileEfficient and practical catalyst-free-like dehydrative N-alkylation of amines and sulfinamides with alcohols initiated by aerobic oxidation of alcohols under air, Application of N-(4-Methoxybenzyl)pyridin-2-amine, the publication is Tetrahedron (2016), 72(2), 264-272, database is CAplus.

We developed simple and practical N-alkylation reactions of amines and sulfinamides with primary and secondary alcs. by using only catalytic amounts of air as the initiator without adding any external catalysts. This method has advantages of simple conditions, easy operation, and comparatively wider scope of substrates, providing an efficient and green catalyst-free-like alc.-based dehydrative N-alkylation method. Mechanistic studies revealed that air initiated the reactions by aerobic oxidation of the alcs. to the key initiating aldehydes or ketones in the presence of bases.

Tetrahedron 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, Application of N-(4-Methoxybenzyl)pyridin-2-amine.

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

Liu, Zhen Gang published the artcileZrCl₄/Hantzsch 1,4-dihydropyridine as a new and efficient reagent combination for the direct reductive amination of aldehydes and ketones with weakly basic amines, Application of N-(4-Methoxybenzyl)pyridin-2-amine, the publication is Chinese Chemical Letters (2007), 18(4), 458-460, database is CAplus.

ZrCl₄/Hantzsch 1,4-dihydropyridine is a mild and highly efficient reagent combination for the direct reductive amination. Weakly basic amines such as anilines substituted by electron-withdrawing group and heteroaromatic amines can be reductively alkylated with electron rich aldehydes and ketones under mild conditions to form the secondary amines in excellent yields.

Chinese Chemical 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, Application of N-(4-Methoxybenzyl)pyridin-2-amine.

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

Sunagawa, Genshun published the artcileDecomposition of benzylamine derivatives. II, SDS of cas: 52818-63-0, the publication is Yakugaku Zasshi (1952), 1570-4, database is CAplus.

cf. C.A. 46, 11210c. 2-Aminopyrimidine (I) (15 g.), 8.7 g. HCO₂H, and 18.4 g. BzH, heated 21 hrs. at 150-60°, cooled, extracted with 80 ml. dilute HCl, the aqueous layer washed with Et₂O, adjusted to pH 7-8, and the precipitate recrystallized from alc. give 18.5 g. 2-benzylaminopyrimidine (II), m. 82.5-3.5°; similarly are prepared the 2-(p-chlorobenzylamino)- (III), m. 127-8°, and 2-(p-nitrobenzylamino)pyrimidine (IV), m. 153-4°. Heating 10 g. p-MeOC₆H₄CHO, 9 g. 2-formamidopyrimidine, and 10 ml. (CH₂OH)₂ 8 hrs. at 170-80° and extracting the product as in the preparation of II gives 14.9 g. 2-(p-methoxybenzylamino)pyrimidine (V), m. 108-9°; 2-(p-MeOC₆H₄CH₂NH)C₅H₄N (VI) m. 124°; 33.2 g. PhNH₂, 10.5 g. NaHCO₃, and 10 ml. water heated with 15.7 g. p-MeOC₆H₄CH₂Cl, cooled, and the product extracted with Et₂O, washed with saturated NaCl solution, and distilled gave 16.6 g. p-MeOC₆H₄CH₂NHPh (VII), b_2.5 170-7°, m. 64-5° (from alc.); reaction of NaNH₂ and II, and treatment of the Na salt with Me₂NCH₂CH₂Cl gave p-RC₆H₄CH₂NR’R” [(VIII), R = H, R’ = 2-pyrimidyl (IX), R” = Me₂NCH₂CH₂ (X)] (XI), b₁₀ 180-4° (HCl salt, m. 204-5°); similarly, III gives VIII (R = Cl, R’ = IX, R” = X) (XII), b₃ 185-90° (HCl salt, m. 163-4°). Treating 22.5 g. anisaldoxime in 94% alc. and 170 ml. water with 60 g. Zn powder and 160 ml. 50% AcOH dropwise, heating 3 hrs. at 30-40°, cooling, alkalinizing and steam-distilling gave 20 g. p-MeOC₆H₄CH₂NH₂.HCl (XIII), m. 230-1°; heating 7.8 g. XI and 3.1 g. Me₂NCH₂CH₂Cl 1 hr. at 100°, alkalinizing, extracting with Et₂O, and distilling gave 2.2 g. (VIII, R = MeO, R’ = H, R” = X), b₁₇ 173-5° (HCl salt, m. 192-3°). Heating II, XI.HCl, and XIII, resp. with 10% HCl 5 hrs. gave unchanged raw materials; 10 g. VI yielded 0.7 g. 2-H₂NC₆H₄N (XIV), m. 57°, and 0.9 g. (p-MeOC₆H₄)₂CH₂ (XV), m. 52° (test for the presence of HCHO was pos.); 10 g. V gave 0.05 g. XV and 1.2 g. XIV; 10 g. VII gave 0.1 g. XV, HCHO, and 0.7 g. PhNH₂, b₁₀ 66° (benzoylated to 1.3 g. C₁₃H₁₁ON, m. 161°).

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 C11H22N2O4, SDS of cas: 52818-63-0.

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

Li, Liantao published the artcileSynthesis and pharmacological activity of fluorescent histamine H₁ receptor antagonists related to mepyramine, Name: N-(4-Methoxybenzyl)pyridin-2-amine, the publication is Bioorganic & Medicinal Chemistry Letters (2003), 13(7), 1245-1248, database is CAplus and MEDLINE.

Fluorescently labeled histamine H₁ receptor antagonists were synthesized starting from N-demethylmepyramine by introduction of ω-aminoalkyl chains (2-8 methylene groups in length) followed by derivatization of the terminal NH₂ group with various fluorophores (fluorescein, naphthofluorescein, rhodamine, tetramethylrhodamine, BODIPY, dansyl, and nitrobenzoxadiazole (NBD)). On the isolated guinea pig ileum and in a Ca²⁺ assay on U373MG human glioblastoma cells the highest H₁ antagonistic activities were found in 5- and 6-carboxyfluorescein labeled compounds with hexa- and octamethylene spacers and in an analogous NBD-aminohexanoyl derivative (pA₂ or pK_B values in the range: 8.3-9.0; compared to 9.3-9.4 for mepyramine).

Bioorganic & Medicinal Chemistry 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, Name: N-(4-Methoxybenzyl)pyridin-2-amine.

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

Kaye, Irving Allan published the artcileReductive alkylation of 2-aminopyridine and 2-aminopyrimidine, Safety of N-(4-Methoxybenzyl)pyridin-2-amine, the publication is Recueil des Travaux Chimiques des Pays-Bas et de la Belgique (1952), 309-17, database is CAplus.

Reductive alkylation of amines with aldehydes and HCO₂H gives better yields of purer products than alkylation with the corresponding bromides and condensing agent. Method A: procedure of Tschitschibabin and Knunianz, C.A. 26, 1932, without significant modification. Method B: 2-C₅H₄NNH₂ (I) or 2-aminopyrimidine (II) (0.5 mol.) and 0.5 mol. aldehyde (III) in 125 ml. 85-90% HCO₂H, were refluxed 20 hrs., poured onto ice, treated with H₂O containing 125 g. NaOH, the mixture was extracted with CHCl₃, and the extract dried over K₂CO₃, concentrated, and distilled in vacuo (the b.ps. listed may be too high because rapid distillation was necessary to prevent crystallization in the side arm of the flask). The products could be used directly, but more conveniently after crystallization from Me₂CHOH (IV) or C₆H_6^–hexane (V). Method C: To I or II and III (1 mol. each) in 125 ml. cumene, refluxed (about 2 hrs.) until the volume of H₂O distilled was constant, was added 108 g. 85-90% HCO₂H (CO₂ was evolved), the solution refluxed 12-24 hrs., concentrated in vacuo, and the residue distilled The following intermediate imine N-derivatives of 2-aminopyridine were isolated (after refluxing with cumene alone) by vacuum distillation: 89% p-chlorobenzylidene (VI), b_0.5 122.5-5°; 89% p-methoxybenzylidene (VII), b_0.6 147-8°, m. 55-7.5° (from MeOH); 95% 3,4-dimethoxybenzylidene (VIII), b_0.2 148-53°; 71% 2-thienylidene, b_0.03 110-12°; 76% furfurylidene (IX), b_0.05 109-13°, m. 52-5° (from (Me₂CH)₂O) (crystallization from Me₂CHOAc converted IX to 2,2′-(furfurylidenediimino)bipyridine, m. 82.5-4°); 93% 3,4-methylenedioxybenzylidene (X), b_0.5 152-3°, m. 99.5-100° (from heptane); 81% 2,3-dimethoxybenzylidene, b_0.09 130-9°; and 73% benzylidene, b₂₂ 174-85° (yellow liquid from which, even when it was kept in a glass-stoppered bottle, precipitated 2,2′-(benzylidenediimino)bi-pyridine, m. 103-5°). To 95.1 g. II and 106.1 g. BzH refluxed 3 hrs. in 200 ml. cumene was added 200 ml. IV and the solution cooled and filtered to give 86% 2,2′-(benzylidenediimino)bipyrimidine (XI), m. 213-15°. The N-benzylidene derivative of II was prepared in poor yield when Ph₂CH₂ was the solvent, or when XI was heated above its m.p. Method D: To 94.1 g. I in 900 ml. refluxing absolute C₆H₆ was added (3 hrs.) 23 g. LiNH₂, then (dropwise) 161 g. p-ClC₆H₄CH₂Cl in 100 ml. C₆H₆, and the mixture refluxed 16 hrs., cooled, washed, concentrated, and distilled, giving 62% 2-(p-chlorobenzylamino)pyridine (XII), b_0.08 133-40° (crystallization from V gave 52% solid, m. 96-8.5°). The following amines, RNHCH₂R’, were prepared [m.p. (from IV unless otherwise specified), procedures used, length of reflux (hrs.), b.p. (°/mm.), and yield (%), resp., given]: When R = 2-pyridyl and R’ = Ph: 97-8°; A, 8, -, 52; A, 94, -, 58; B, 168, 181-2°/12, 68; C, 20, 133-4°/0.12, 88. p-ClC₆H₄: 103-4° (from V); C, -, 136-8°/0.02, 79. p-MeOC₆H₄ (XIII): 124-5°; B, 20, 153°/0.1, 54; C, 20, 143-6°/0.06, 87. 2,3-(MeO)₂C₆H₃: 83.5-4.5°; A, 94, -, 67; B, 168, 142-6°/0.1, 73; C, 24, 156-7°/0.1, 81. 3,4-(MeO)₂C₆H₃ (XIV): 104.5°; B, 20, 156°/0.08, 62; C, 20, 173-6°/0.08, 83. 3,4-CH₂O₂C₆H₃: 97-8°; B, 20, 148°/0.12, 53; C, 24, 158-9°/0.08, 92. 2-Thienyl: 80-1°; C, 15, 120-5°/0.02, 61. When R = 2-pyrimidyl and R’ = Ph: 82.5-3°: A, 94, -, 40; B, 168, 179-84°/13, 51; B, 17, 105°/0.08, 53. p-MeOC₆H₄: 108.5-9.5° (from MeOH); B, 20, 150°/0.3, 45; B, 71, 148°/0.3, 29; C, 12, 150-2°/0.2, 42. 2,3-(MeO)₂C₆H₃: 94-5°; A, 94, -, 55; B, 168, 208-16°/19, 43; B, 17, 136°/ 0.12, 72; C, 12, 162-3°/0.4, 63. 3,4-(MeO)₂C₆H₃ (XV): 123.5-4.5° (from MeOH); A, 20, -, 37; B, 19, 176-87°/0.5, 39; C, 12, 155-63°/0.16, 45 [HCl salt, m. 159-60° (from EtOH)]. 3,4-CH₂O₂C₆H₃: 118-18.5°; A, 16.5, -, 39; A, 20, -, 42; B, 19, 156-63°/0.1, 41; C, 20, 168-70°/0.5, 47 [HCl salt, m. 172.5-3.5° (from EtOH)]. No evidence of ability to retard the growth of sarcoma 180 in rats was shown by VI, VII, VIII, IX, X, XII, XIII, XIV, or XV.

Recueil des Travaux Chimiques des Pays-Bas et de la Belgique 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, Safety of N-(4-Methoxybenzyl)pyridin-2-amine.

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

Chichibabin, A. E. published the artcileAction of aldehydes on α-aminopyridine and on α-dimethylaminopyridine, Related Products of ethers-buliding-blocks, the publication is Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen (1931), 2839-42, database is CAplus.

In the action of HCHO on α-aminopyridine (1), 2 reactions take place simultaneously, condensation to a dipyridyl derivative and methylation of the amino group, the end product being p,p’-tetra methyldiaminodipyridylmethane (C. A. 24, 1642). It seemed of interest to study the behavior of other aldehydes toward I under these conditions. With aromatic aldehydes in HCO₂H there is no condensation, only a reaction analogous to the above methylation but differing from it in that only 1 H atom of the amino group seems to be replaced by the aromatic residue because the primarily formed Schiff base is at once reduced; secondary amines can be obtained in excellent yield by this method. The o-substituted derivatives of BzH studied (o-NO₂, o-HO) do not react with I under these conditions. BzH, heated with α-C₅H₄NNMe₂ (II) and ZnCL₂, reacts like BzH with PhNMe₂, giving phenylbis(α-dimethylaminopyridyl)methane (III), which is oxidized by PbO₂ in acid solution to the carbinol (IV). α-Benzylaminopyridine, m. 94°, is obtained in 90% yield from I in anhydrous HCO₂H refluxed with BzH. α-(p-Methoxybenzylamino)pyridine, from I and anisaldehyde (80-5% yield), m. 128°. α-(3,4-Methylenedioxybenzylamino)-pyridine (70%), m. 99-100°. α-Formylaminopyridine, from equimol. amounts of I and anhydrous HCO₂H carefully heated in a Claisen flask until the formation of water ceased, b₁₅161-2°, m. 71°. III (6 g. from 10 g. II), m. 130-1°, soluble in H₂SO₄ without color. IV, yellowish, m. 123-4°, soluble in concentrated H₂SO₄ with blood-red and in HCl with deep red color, water destroying the color, which, however, is restored by concentrated acids, although the simple salts cannot be obtained in colored form.

Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen 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, Related Products of ethers-buliding-blocks.

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

Yigit, Murat published the artcileRuthenium(II)-NHC-catalyzed (NHC = perhydrobenzimidazol-2-ylidene) alkylation of amines using the hydrogen borrowing methodology under solvent-free conditions, Formula: C13H14N2O, the publication is Transition Metal Chemistry (Dordrecht, Netherlands) (2019), 44(6), 565-573, database is CAplus.

New ruthenium(II) complexes with N-heterocyclic carbene ligand were synthesized by transmetalation reactions between silver(I) N-heterocyclic carbene complexes and [RuCl₂(p-cymene)]₂. The complexes were characterized by physicochem. and spectroscopic methods. These ruthenium complexes were applied to the N-monoalkylation of aromatic amines with a wide range of primary alcs. under solvent-free conditions using the hydrogen borrowing strategy. The catalytic reactions using all ruthenium complexes resulted in N-monoalkylated products with high selectivities using furfuryl alc. as the alkylating agent.

Transition Metal Chemistry (Dordrecht, Netherlands) 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 C40H35N7O8, Formula: C13H14N2O.

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