1125-90-2

Usage

InChI:InChI=1/C9H11NO/c1-10-7-8-5-3-4-6-9(8)11-2/h3-7H,1-2H3/b10-7+

Upstream product

• 135-02-4 ortho-anisaldehyde 
• 74-89-5 methylamine 
• 33499-30-8 (Z)-C-(2-methoxyphenyl)-N-methyl-nitrone 
• 593-51-1 methylamine hydrochloride 
• 65398-48-3 methylammonium N-methylcarbamate 

Downstream Products

• 126300-62-7 {2-Methoxy-1-(2-methoxy-phenyl)-3-[1-trimethylsilanyl-meth-(E)-ylidene]-hex-5-enyl}-methyl-amine 
• 887830-44-6 C₁₇H₁₉NO₂ 
• 887830-45-7 C₁₇H₂₁NO₂ 
• 339001-35-3 C₁₇H₁₉NO 
• 1144106-37-5 C₁₃H₁₅NO₂ 
• 33499-30-8 N-(2-methoxybenzylidene)methanamine N-oxide 
• 79865-91-1 o-methoxybezylidenedimethylimmonium iodide 
• 76086-84-5 4-[(2-Methoxy-phenyl)-methylamino-methyl]-5-methyl-2-phenyl-2,4-dihydro-pyrazol-3-one 
• 104178-98-5 [1-(2-methoxy-phenyl)-propyl]-methyl-amine 

Relevant academic research and scientific papers

Photosensitized Electron-Transfer Reaction of 3-Aryl-2-methyloxaziridine: Direct Deoxygenation from the Isomeric Arylnitrone

Photosensitized electron-transfer reactions of 3-aryl-2-methyloxaziridines gave mainly the corresponding benzaldehydes, whereas the isomeric nitrones gave imines as well as aldehydes.Deoxygenation of the nitrone occurred via the nitrone cation radical under the reaction conditions.An aryl substituent effect on the reaction and isomerizations of both cation radicals are also discussed.

Synthesis of N-methyl imines in the presence of poly(N-vinylpyridine) as a reusable solid base catalyst by a mechanochemical process

The synthesis of N-methyl imines was performed in the presence of catalytic amounts of poly(4-vinylpyridine) in high yields and rapidly at room temperature by a ball milling process. This new method has some advantages including good yields for relatively unreactive carbonyl compounds and short reaction times as well as being green in terms of avoiding the use of toxic reagents and solvents. The major advantage of this process is that the catalyst can be easily regenerated and reused several times without any significant loss of activity.

Stable carbamate pathway towards organic-inorganic hybrid perovskites and aromatic imines

Methyl ammonium methyl carbamate (MAC), formulated as CH3NH3+CH3NHCO2-, was synthesized by reacting liquid methylamine with supercritical CO2, and its structure was refined by single-crystal X-ray diffraction. MAC is a white crystalline salt and is as reactive as methylamine, and is a very efficient alternative to toxic methylamine. We were able to produce hybrid perovskite MAPbI3 (MA = methyl ammonium) by grinding MAC with PbI2 and I2 at room temperature, followed by storing the mixed powder. Moreover, this one-pot method is easily scalable for the large-scale synthesis of MAPbI3 in a small vessel. We have also investigated the reactivity of MAC towards aromatic aldehydes in the absence of solvent. The solventless reactions afforded imines as exclusive products with over 97% yield, which show higher selectivity than the methylamine-based synthesis. Complete conversions were typically accomplished within 3 h at 25 °C. The results of this study emphasize the importance of solid carbamates such as MAC to develop an environmentally friendly process for the synthesis of various amine-based materials on the industrial scale.

Enantioselective Reductive Coupling of Imines Templated by Chiral Diboron

We herein report a general, practical, and highly efficient method for asymmetric synthesis of a wide range of chiral vicinal diamines via reductive coupling of imines templated by chiral diboron. The protocol features high enantioselectivity and stereospecificity, mild reaction conditions, simple operating procedures, use of readily available starting materials, and a broad substrate scope. The method signifies the generality of diboron-enabled [3,3]-sigmatropic rearrangement.

Epoxide-Mediated Stevens Rearrangements of α-Amino-Acid-Derived Tertiary Allylic, Propargylic, and Benzylic Amines: Convenient Access to Polysubstituted Morpholin-2-ones

A new strategy has been established for the synthesis of polysubstituted morpholin-2-ones through Stevens rearrangements of tertiary amines via in situ activation with epoxides. A range of α-amino acid-derived tertiary allylic, propargylic, and benzylic amines reacted with epoxides in the presence of zinc halide catalysts to afford structurally diverse allyl-, allenyl-, and benzyl-substituted morpholin-2-ones, respectively, in moderate-to-good yields with high regioselectivity. The process involves [2,3]- and [1,2]-Stevens rearrangements of quaternary ammonium ylide intermediates and constitutes a very convenient method to prepare polysubstituted morpholin-2-ones through tandem formation of C?N, C?O, and C?C bonds. Moreover, replacing epoxides with aziridines permitted the synthesis of polysubstituted piperazin-2-ones.

Mechanosynthesis of N-methyl imines using recyclable imidazole-based acid-scavenger: In situ formed ionic liquid as catalyst and dehydrating agent

1,1′-(1,4-Butanediyl)bis(imidazole) was prepared by a modified method and its application as an efficient promoter was demonstrated for the mechanosynthesis of N-methyl imines using ball milling as a non-conventional process under solvent-free conditions. In this new protocol design, the bis-imidazole acted as a recyclable acid-scavenging agent. This efficient approach to the N-methyl imines displays a combination of the synthetic virtues of a non-conventional condensation reaction with ecological benefits and convenience of a facile mechanosynthetic process. The current method has advantages such as reduced waste by avoiding solvent, exclusion of hazardous materials during the reaction, elimination of handling an anhydrous gas in an evacuated container or a solution of methylamine in ethanol, good yields for relatively unreactive benzaldehydes containing electron-donating substituents, short reaction times, and metal- and acid-free conditions. Furthermore, the promoter was easily regenerated and reused several times with no significant loss of activity.

Unusually Reactive Cyclic Anhydride Expands the Scope of the Castagnoli-Cushman Reaction

In the course of synthesizing and testing various "azole-including" cyclic anhydrides in the Castagnoli-Cushman reaction with imines, a remarkably reactive, pyrrole-based anhydride has been identified. It displayed a remarkably efficient reaction with N-alkyl and N-aryl imines, in particular, with "enolizable" α-C-H imines which typically fail to react with a majority of known cyclic anhydrides. The reactivity of this anhydride has been justified by an efficient resonance stabilization of its enol form. This finding expands the existing arsenal of highly reactive cyclic anhydrides and further confirms the importance of anhydride enolization for an efficient Castagnoli-Cushman reaction.

Simple and efficient one-pot solvent-free synthesis of N-methyl imines of aromatic aldehydes

A one-pot solvent-free synthesis of N-methyl imines in good to excellent yields was performed by grinding together aromatic aldehydes and methylamine hydrochloride in the presence of a base. The best yields were achieved when an excess of methylamine hydrochloride and inexpensive sodium hydrogen carbonate was used (usually in a molar ratio ArCHO/CH3NH2· HCl/NaHCO3 = 1:5:5), allowing the reaction to proceed for 1 h (in the case of aromatic aldehydes containing electron-withdrawing substituents) or overnight (in the case of electron-rich aldehydes). After a simple work-up (extraction with diethyl ether) the obtained products were mostly pure enough for spectral characterization. In this way, 31 N-methyl imines were prepared, among which eight were synthesized for the first time. Their structures were elucidated by spectral means (1H- and 13C-NMR, IR, MS) whenever it was possible. In the case of salicylaldehyde and 4-chlorobenzaldehyde, the synthesis of the corresponding imines was also conducted on a gram-scale with a 72% and 84% isolated yield, respectively. The present approach not only provides good to high yields, but also eliminates the disadvantages of the traditional synthesis of N-methyl imines, such as the use of hazardous solvents and more or less expensive catalysts and the necessity of work/handling with an anhydrous gas in pressurized containers.

4-Phenyl tetrahydroisoquinolines as dual norepinephrine and dopamine reuptake inhibitors

Novel 4-phenyl tetrahydroisoquinolines that inhibit both dopamine and norepinephrine transporters were designed and prepared. In this Letter, we describe the synthesis, in vitro activity and associated structure-activity relationships of this series. We also report the ex vivo NET occupancy of a representative compound, 41.

Highly enantioselective synthesis of tetrahydroquinolines via cobalt(II)-catalyzed tandem 1,5-hydride transfer/cyclization

A chiral catalyst prepared from N,N′-dioxide and Co(BF 4)2·6H2O was applied in the asymmetric hydride transfer initiated cyclization reaction, giving optically active tetrahydroquinolines in good yields with high enantioselectivities under mild reaction conditions. Meanwhile, in light of the absolute configuration of the product, a possible working model was proposed to explain the origin of the activation and asymmetric induction.