97113-39-8

Upstream product

• 537-92-8 3-Methylacetanilide 
• 4949-69-3 4-iodo-3-methylaniline 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 
• 5326-38-5 2-iodo-5-nitrotoluene 

Downstream Products

• 57772-58-4 5-acetylamino-2-iodo-benzoic acid 
• 1234513-17-7 C₁₇H₁₆N₂O 
• 97113-23-0 (2-Chloro-3-methyl-6-nitro-4-piperidin-1-yl-benzylamino)-acetic acid ethyl ester 
• 96336-70-8 (2-Amino-5-methyl-4-piperidin-1-yl-benzylamino)-acetic acid ethyl ester 
• 97112-74-8 5-Methyl-2-nitro-4-piperidin-1-yl-benzonitrile 
• 97113-19-4 5-Methyl-2-nitro-4-piperidin-1-yl-benzylamine 
• 97112-60-2 4-iodo-5-methyl-2-nitrobenzonitrile 
• 335349-58-1 4-iodo-5-methyl-2-nitroaniline 

Relevant academic research and scientific papers

Complementary Site-Selective Halogenation of Nitrogen-Containing (Hetero)Aromatics with Superacids

Site-selective functionalization of arenes that is complementary to classical aromatic substitution reactions remains a long-standing quest in organic synthesis. Exploiting the generation of halenium ion through oxidative process and the protonation of the nitrogen containing function in HF/SbF5, the chlorination and iodination of classically inert Csp2?H bonds of aromatic amines occurs. Furthermore, the superacid-promoted (poly)protonation of the molecules acts as a protection, favoring the late-stage selective halogenation of natural alkaloids and active pharmaceutical ingredients.

A para-C–H Functionalization of Aniline Derivatives via In situ Generated Bulky Hypervalent Iodinium Reagents

A practical para-C-H functionalization of aniline derivatives has been developed using an in situ generated bulky hypervalent iodinium reagent. Para-iodo, bromo, chloro, nitro, trifluormethyl aniline derivatives can be obtained efficiently, in many cases in 10 min in a transition metal-free manner. Medicinal chemicals or intermediates can be purified without column chromatography or recrystallization, which significantly reduces the waste and simplifies the work-up process.

Selective Halogenation Using an Aniline Catalyst

Electrophilic halogenation is used to produce a wide variety of halogenated compounds. Previously reported methods have been developed mainly using a reagent-based approach. Unfortunately, a suitable "catalytic" process for halogen transfer reactions has yet to be achieved. In this study, arylamines have been found to generate an N-halo arylamine intermediate, which acts as a highly reactive but selective catalytic electrophilic halogen source. A wide variety of heteroaromatic and aromatic compounds are halogenated using commercially available N-halosuccinimides, for example, NCS, NBS, and NIS, with good to excellent yields and with very high selectivity. In the case of unactivated double bonds, allylic chlorides are obtained under chlorination conditions, whereas bromocyclization occurs for polyolefin. The reactivity of the catalyst can be tuned by varying the electronic properties of the arene moiety of catalyst.

Pd-catalyzed ortho-selective oxidative coupling of halogenated acetanilides with acrylates

Coupling of different halogenated acetanilides with acrylates using Pd-catalyzed ortho-selective C-H bond activation is reported. The yields of coupled products are low to high depending on the substrate. In general, arenes with electron-rich substituents like methoxy and methyl groups gave higher yields of the coupled products. The presence of the halogen substituent did not interfere with the activation process under these conditions.

Palladium-catalyzed sequential alkylation - Alkenylation reactions and their application to the synthesis of fused aromatic rings

The synthesis of fused aromatic carbocycles from aryl iodides and difunctional acceptors is outlined. This methodology is based on a palladium-catalyzed aromatic substitution followed by an intramolecular Heck sequence. Under the optimized conditions (Pd(OAc)2 (10 mol %), tri-2-furylphosphine (20-30 mol %), norbornene (2 equiv), Cs2CO3 (2 equiv), CH3CN, reflux), bromoenoates react with aryl iodides bearing numerous substituents (F, Cl, CF3, Me, etc.). The expanded description of our initial work as well as the use of polysubstituted aryl iodides is described.

Oxidative Iodination of Aromatic Amides Using Sodium Perborate or Hydrogen Peroxide with Sodium Tungstate

Hydrogen peroxide or sodium perborate in the presence of a sodium tungstate catalyst are shown to be cheap oxidants for the iodination of aromatic amides using potassium iodide as the source of the iodine.

Halogenation Using Quaternary Ammonium Polyhalides. XVII. Iodination of Acetanilide Derivatives with Benzyltrimethylammonium Dichloroiodate and Zinc Chloride

The reaction of acetanilide derivatives with benzyltrimethylammonium dichloroiodate in acetic acid in the presence of ZnCl2 at room temperature or at 70 deg C gave iodo-substituted acetanilide derivatives in good yields.