26488-93-7

Usage

Chemical Properties

Light Brown Solid

InChI:InChI=1/C8H8ClNO2/c1-5(11)10-7-4-6(9)2-3-8(7)12/h2-4,12H,1H3,(H,10,11)

Upstream product

• 89-64-5 p-chloro-o-nitrophenol 
• 108-24-7 acetic anhydride 
• 95-85-2 2-hydroxy-5-chloro-aniline 
• 463-51-4 Ketene 
• 60386-78-9 4-chloro-2-nitrophenyl acetate 
• 87049-66-9 2'-amino-5'-chloroacetanilide 
• 614-80-2 2-(acetylamino)phenol 
• 36637-30-6 O-(4-chlorophenyl)hydroxylamine 
• 220464-84-6 (p-chloro-N-phenoxy)phthalimide 
• 1679-18-1 4-Chlorophenylboronic acid 
• 123-54-6 acetylacetone 
• 75-36-5 acetyl chloride 
• 3964-52-1 2-chloro 4-aminophenol 
• 5443-33-4 N-(5-chloro-2-nitrophenyl)acetamide 

Downstream Products

• 67944-06-3 acetic acid-(5-chloro-3-diethylaminomethyl-2-hydroxy-anilide) 
• 860675-48-5 acetic acid-[5-chloro-2-(2-diethylamino-ethoxy)-anilide] 
• 19219-99-9 2-methyl-5-chlorobenzoxazole 
• 88-23-3 2-amino-4-chlorophenol-6-sulfonic acid 
• 156016-33-0 acetic acid-(5-chloro-2-hydroxy-3-nitro-anilide) 
• 676131-84-3 2-acetylamino-4-chloro-6-(2-chlorobenzoyl)phenol 
• 106612-63-9 2-acetylamino-6-benzoyl-4-chlorophenol 
• 21312-94-7 2-acetylamino-6-acetyl-4-chlorophenol 
• 96079-86-6 5-chloro-2-(2-diethylamino-ethoxy)-aniline 
• 28763-40-8 N-(5-Chloro-2-oxiranylmethoxy-phenyl)-acetamide 
• 868408-04-2 N-(5-chloro-2-{2-[7-(4-fluorobenzyl)-3-oxa-7,9-diazabicyclo[3.3.1]non-9-yl]-2-oxoethoxy}-phenyl)acetamide 
• 1221498-22-1 N-(2-(allyloxy)-5-chlorophenyl)acetamide 
• 676131-85-4 2-acetylamino-4-chloro-6-(4-chlorobenzoyl)phenol 
• 1296885-50-1 N-[5-chloro-2-(3-hydroxy-3-methyl-but-1-ynyl)-phenyl]-acetamide 

Relevant academic research and scientific papers

Iron(III)-Mediated Nucleophilic Halogenation of Phenols Using an Amido Directing Group

A regioselective and nucleophilic halogenation of electron-rich amidophenols was realized in the presence of Fe(III) reagents and amido-directing groups. Halides could be sequentially introduced to specific positions to form mono-, di- and mixed di- halogenated amidophenols. Furthermore, this protocol provides new methods for the syntheses of IKK2 inhibitor (IMD-0354), muscle relaxant (Chlorzoxazone) and related derivatives.

Antimalarial Benzimidazole Derivatives Incorporating Phenolic Mannich Base Side Chains Inhibit Microtubule and Hemozoin Formation: Structure-Activity Relationship and in Vivo Oral Efficacy Studies

A novel series of antimalarial benzimidazole derivatives incorporating phenolic Mannich base side chains at the C2 position, which possess dual asexual blood and sexual stage activities, is presented. Structure-activity relationship studies revealed that the 1-benzylbenzimidazole analogues possessed submicromolar asexual blood and sexual stage activities in contrast to the 1H-benzimidazole analogues, which were only active against asexual blood stage (ABS) parasites. Further, the former demonstrated microtubule inhibitory activity in ABS parasites but more significantly in stage II/III gametocytes. In addition to being bona fide inhibitors of hemozoin formation, the 1H-benzimidazole analogues also showed inhibitory effects on microtubules. In vivo efficacy studies in Plasmodium berghei-infected mice revealed that the frontrunner compound 41 exhibited high efficacy (98% reduction in parasitemia) when dosed orally at 4 × 50 mg/kg. Generally, the compounds were noncytotoxic to mammalian cells.

Chiral N,N Ligands Enabling Palladium-Catalyzed Enantioselective Intramolecular Heck–Matsuda Carbonylation Reactions by Sequential Migratory and CO Insertions

Unprecedented enantioselective intramolecular Heck carbonylation reactions of arenediazonium salts were enabled by a chiral N,N ligand. This reaction constitutes the first enantioselective Heck carbonylation that proceeds through migratory insertion followed by CO insertion. The enantioenriched functionalized dihydrobenzofurans were obtained in good to high yields and enantiomeric ratios of up to 98:2 under mild and operationally simple reaction conditions.

Cp?Rh(III)/Bicyclic Olefin Cocatalyzed C-H Bond Amidation by Intramolecular Amide Transfer

A bicyclic olefin was discovered as a cocatalyst in a Cp?Rh(III)-catalyzed C-H bond amidation proceeding by an intramolecular amide transfer in N-phenoxyacetamide derivatives. Combining experimental and theoretical studies, we propose that the olefin promotes a Rh(III) intermediate to undergo oxidative addition into the O-N bond to form a Rh(V) nitrenoid species and subsequently direct the nitrenoid to add to the ortho position. The amide directing group plays a dual role as a cleavable coordinating moiety as well as an essential coupling partner for the C-H amidation. This methodology was successfully applied to the late-stage diversification of natural products and a marketed drug under mild conditions.

Synthesis of benzoxazoles from 2-aminophenols and β-diketones using a combined catalyst of br?nsted acid and copper iodide

Cyclization reactions of 2-aminophenols with β-diketones catalyzed by a combination of Br?nsted acid and CuI are presented. Various 2-substituted benzoxazoles were obtained through these reactions. Different substituents such as methyl, chloro, bromo, nitro, and methoxy on 2-aminophenol are tolerated under the optimized reaction conditions.

2-Substituted-2,3-dihydro-1 H -quinolin-4-ones via acid-catalyzed tandem rupe rearrangement-donnelly-farrell ring closure of 2-(3′-hydroxypropynyl) anilines

A range of 2-substituted 2,3-dihydro-1H-quinolin-4-ones have been synthesized from anilines by a two-step process involving Sonogashira coupling with a propargyl alcohol then acid-catalyzed cyclization of the resulting 2-(3′-hydroxypropynyl)anilines. The cyclization reaction appears to proceed via regioselective rearrangement of the propargyl alcohol to an α,β-unsaturated ketone (Rupe rearrangement) and then 6-endo-trig ring closure (Donnelly-Farrell cyclization). The isolation of the α,β-unsaturated ketone intermediate in one example supports this pathway. Georg Thieme Verlag Stuttgart.

The first intramolecular Heck-Matsuda reaction and its application in the syntheses of benzofurans and indoles

In this Letter, we report, for the first time, the development of an efficient method for the intramolecular Heck reaction of arenediazonium salts in the synthesis of benzofuran and indole derivatives. In addition, this methodology allowed the synthesis of a series of dihydrobenzofuran acetic acid derivatives via a domino Heck-Matsuda coupling-carbonylation reaction.

Regioselective syntheses of 2- and 4-formylpyrido[2,1-b]benzoxazoles

o-Acetaminophenols (2) reacted with Vilsmeier reagent under Meth-Cohn conditions to yield 2-formylpy-rido[2,l-6]benzoxazoles (5) unexpectedly besides the known compounds 2-(benzoxazol-2′-yl)-3-dimethylaminoacroleins (4). Refluxing 4 in acetic anhydride gave 4-formylpyrido[2,l-6]benzoxazoles (6), an isomer of 5. Both 5a and 6a were structurally characterized by X-ray crystallography. A mechanism for the formation of 5 involving sequential chlorination, dimerization, intramolecular elimination of HC1 to form the oxazole ring, formylation twice, and regioselective intramolecular nucleophilic cyclization to construct the pyridone ring is proposed.

Stable crystalline form of bifeprunox mesylate, dosage forms thereof and methods for using same

The present disclosure provides novel pharmaceutical compounds and methods for making the same, novel pharmaceutical dosage forms and methods for making the same, and methods for using said compounds and dosage forms to treat and prevent diseases and/or d

Stable crystalline form of bifeprunox mesylate (7-[4-([1,1'-biphenyl]-3-ylmethyl)-1-piperazinyl]-2(3H)-benzoxazolone monomethanesulfonate)

The invention relates to a stable polymorphic form of the compound 7-[4-([1,1′-biphenyl]-3-ylmethyl)-1-piperazinyl]-2(3H)-benzoxazolone monomethanesulfonate (INNM bifeprunox mesylate), a method for the preparation of said polymorphic form and its use in p