122334-36-5

Usage

Uses

N-Methoxy-N,4-dimethylbenzamide is used in the synthesis of Fingolimod (F342045)

InChI:InChI=1/C10H13NO2/c1-8-4-6-9(7-5-8)10(12)11(2)13-3/h4-7H,1-3H3

Upstream product

• 1613-85-0 N-methyl-N-(4-methylbenzoyl)hydroxylamine 
• 6214-19-3 methyl p-methoxybenzenesulfonate 
• 99-94-5 p-Toluic acid 
• 1117-97-1 N,0-dimethylhydroxylamine 
• 31614-66-1 tributyl(p-tolyl)stannane 
• 30289-28-2 N-methoxy-N-methylcarbamoyl chloride 
• 874-60-2 4-methyl-benzoyl chloride 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 223570-55-6 N-methoxy-N-methyl-2-pyridyl urethane 
• 29829-22-9 S-methyldibenzothiophenium tetrafluoroborate 
• 6638-79-5 N,O-dimethylhydroxylamine*hydrochloride 
• 1062512-43-9 C₆H₁₈N₃O₃P 
• 201230-82-2 carbon monoxide 
• 106-38-7 para-bromotoluene 

Downstream Products

• 1669-33-6 pentyl 4-methylphenyl ketone 
• 402476-17-9 1-p-toluoyl-2-[(trimethylsilyl)ethynyl]benzene 
• 724452-72-6 4-(bromomethyl)-N-methoxy-N-methylbenzamide 
• 51490-06-3 1,2-di-p-tolyl-ethanone 
• 52920-19-1 2-(4-methylbenzoyl)-benzaldehyde 
• 104-85-8 para-methylbenzonitrile 
• 1344201-16-6 2-hydroxy-N-methoxy-N,4-dimethylbenzamide 
• 104-87-0 4-methyl-benzaldehyde 
• 18370-11-1 N-methyl-p-methylbenzamide 
• 73119-33-2 (1,3-dithian-2-yl)(p-tolyl)methanone 
• 589-18-4 4-Methylbenzyl alcohol 
• 1258539-07-9 2,2-dimethyl-N-[4-(4-methylbenzoyl)pyridin-3-yl]propanamide 
• 127446-46-2 2-<(2,2-Dimethyl-1-oxopropyl)amino>-β-hydroxy-β-(4-methylphenyl)-3-pyridinepropanoic Acid, 1,1-Dimethylethyl Ester 
• 127446-47-3 4-(4-Methylphenyl)-1,8-naphthyridin-2-one 

Relevant academic research and scientific papers

Efficient palladium-catalyzed aminocarbonylation of aryl iodides using palladium nanoparticles dispersed on siliceous mesocellular foam

A highly dispersed nanopalladium catalyst supported on mesocellular foam (MCF), was successfully used in the heterogeneous catalysis of aminocarbonylation reactions. During the preliminary evaluation of this catalyst it was discovered that the supported palladium nanoparticles exhibited a "release and catch" effect, meaning that a minor amount of the heterogeneous palladium became soluble and catalyzed the reaction, after which it re-deposited onto the support. It's catchy! An efficient palladium-catalyzed protocol for the aminocarbonylation of aryl iodides is reported in which the palladium immobilized on the amino-functionalized mesocellular foam (MCF) was found to operate through a "release and catch" mechanism (see scheme). A very low content of palladium was found in solution upon completion of the reaction and a variety of different aryl iodides were converted to the corresponding amides under mild conditions.

Amide Bond Formation via the Rearrangement of Nitrile Imines Derived from N-2-Nitrophenyl Hydrazonyl Bromides

We report how the rearrangement of highly reactive nitrile imines derived from N-2-nitrophenyl hydrazonyl bromides can be harnessed for the facile construction of amide bonds. This amidation reaction was found to be widely applicable to the synthesis of primary, secondary, and tertiary amides and was used as the key step in the synthesis of the lipid-lowering agent bezafibrate. The orthogonality and functional group tolerance of this approach was exemplified by the N-acylation of unprotected amino acids.

Deoxygenative hydroboration of primary, secondary, and tertiary amides: Catalyst-free synthesis of various substituted amines

Transformation of relatively less reactive functional groups under catalyst-free conditions is an interesting aspect and requires a typical protocol. Herein, we report the synthesis of various primary, secondary, and tertiary amines through hydroboration of amides using pinacolborane under catalyst-free and solvent-free conditions. The deoxygenative hydroboration of primary and secondary amides proceeded with excellent conversions. The comparatively less reactive tertiary amides were also converted to the corresponding N,N-diamines in moderate yields under catalyst-free conditions, although alcohols were obtained as a minor product.

A CO2-Catalyzed Transamidation Reaction

Transamidation reactions are often mediated by reactive substrates in the presence of overstoichiometric activating reagents and/or transition metal catalysts. Here we report the use of CO2as a traceless catalyst: in the presence of catalytic amounts of CO2, transamidation reactions were accelerated with primary, secondary, and tertiary amide donors. Various amine nucleophiles including amino acid derivatives were tolerated, showcasing the utility of transamidation in peptide modification and polymer degradation (e.g., Nylon-6,6). In particular,N,O-dimethylhydroxyl amides (Weinreb amides) displayed a distinct reactivity in the CO2-catalyzed transamidation versus a N2atmosphere. Comparative Hammett studies and kinetic analysis were conducted to elucidate the catalytic activation mechanism of molecular CO2, which was supported by DFT calculations. We attributed the positive effect of CO2in the transamidation reaction to the stabilization of tetrahedral intermediates by covalent binding to the electrophilic CO2

Rhoda-Electrocatalyzed Bimetallic C?H Oxygenation by Weak O-Coordination

Rhodium-electrocatalyzed arene C?H oxygenation by weakly O-coordinating amides and ketones have been established by bimetallic electrocatalysis. Likewise, diverse dihydrooxazinones were selectively accessed by the judicious choice of current, enabling twofold C?H functionalization. Detailed mechanistic studies by experiment, mass spectroscopy and cyclovoltammetric analysis provided support for an unprecedented electrooxidation-induced C?H activation by a bimetallic rhodium catalysis manifold.

Phase-Transfer Catalyzed Asymmetric [4 + 1] Annulations for the Synthesis of Chiral 2,2-Disubstituted Tetrahydrothiophenes

An efficient catalytic asymmetric [4 + 1] reaction, which features the use of simple β-keto esters as one-carbon nucleophiles and 5-succinimidothio-pent-2-enoates as four-atom bielectrophiles, has been developed in the presence of a bifunctional chiral ph

Synthesis of various acylating agents directly from carboxylic acids

A straightforward synthesis of acylating reagents such as Weinreb and MAP amides from aromatic, aliphatic carboxylic acids, and amino acids using PPh3/NBS combination is described. A chemo-selective modification of the carboxylic acid group into Weinreb amide in the presence of more reactive aldehydes and ketones is presented. All reactions were performed at ambient temperature under air using undried commercial grade solvent. Furthermore, the present methodology could be performed at a gram scale under inert-free reaction conditions. In addition, 7-azaindoline amide auxiliary (used for catalytic asymmetric aldol- and Mannich-type reactions), which behaves like Weinreb amide is also synthesized under similar reaction conditions.

Potent Analogues of Abscisic Acid – Identifying Cyano-Cyclopropyl Moieties as Promising Replacements for the Cyclohexenone Headgroup

Synthetic analogues of plant hormone abscisic acid (ABA) bearing a yet unexplored head group motif were prepared based on a combination of agrochemical experience, in vivo hits and structure-based design. It could thus be explored how modifying key parts of ABA's cyclohexenone unit influenced receptor affinity and in vivo efficacy against drought stress in selected crops. Cyano-cyclopropyl groups proved to be suitable replacements of the cyclohexanone moiety leading to ABA analogues with strong activity in vitro and in vivo. Their efficient and versatile synthesis proceeded via Stille or Sonogashira couplings as the key steps. Combining novel cyano-cyclopropyl headgroups with previously identified substituents in the terpenoid side chain afforded the most promising effects against drought stress in crops, particularly canola and wheat.

Mo(CO)6 as a Solid CO Source in the Synthesis of Aryl/Heteroaryl Weinreb Amides under Microwave-Enhanced Condition

The facile transformation of aryl/heteroaryl nonaflates into corresponding amides via Pd-catalyzed aminocarbonylation using Mo(CO)6 as a solid CO source under microwave-enhanced condition is reported. The method was found to be tolerant with respect to a

Palladium-Catalyzed, ortho-Selective C-H Halogenation of Benzyl Nitriles, Aryl Weinreb Amides, and Anilides

A palladium-catalyzed, ortho-selective C-H halogenation methodology is reported herein. The highlight of the work is the highly selective C(sp2)-H functionalization of benzyl nitriles in the presence of activated C(sp3)-H bond, which results in good yields of the halogenated products with excellent regioselectivity. Along with benzyl nitriles, aryl Weinreb amides and anilides have been evaluated for the transformation using aprotic conditions. Mechanistic studies yield interesting aspects with respect to the pathway of the reaction and the directing group abilities.