7073-42-9

Usage

Uses

Used in Pharmaceutical Industry:
3-Chloro-4-Methoxyacetanilide is utilized as an intermediate in the production of anti-inflammatory and analgesic drugs. Its unique structure allows it to be a key component in the development of medications aimed at reducing inflammation and pain.
Used in Organic Chemical Reactions:
As a reagent, 3-Chloro-4-Methoxyacetanilide is employed in various organic chemical reactions, facilitating the synthesis of a range of organic compounds. Its properties make it a useful tool for chemists in the development of new chemical entities.
Used in Synthesis of Complex Organic Molecules:
3-Chloro-4-Methoxyacetanilide also serves as a building block in the synthesis of complex organic molecules. Its structural features contribute to the creation of intricate chemical structures that are vital in numerous applications across different industries.

InChI:InChI=1/C9H10ClNO2/c1-6(12)11-7-3-4-9(13-2)8(10)5-7/h3-5H,1-2H3,(H,11,12)

Upstream product

• 5345-54-0 3-chloro-4-methoxyaniline 
• 51-66-1 4-methoxyacetanilide 
• 75-36-5 acetyl chloride 
• 4920-79-0 2-chloro-4-nitroanisole 
• 631-61-8 ammonium acetate 
• 64-19-7 acetic acid 
• 766-51-8 2-Chloroanisole 
• 108-24-7 acetic anhydride 

Downstream Products

• 3964-54-3 3-chloro-4-hydroxyacetanilide 
• 685534-98-9 3-[2-(acetylamino)-4-chloro-5-methoxyphenyl]-2-(2E)-propenoic acid 
• 119927-90-1 3-chloro-4,4-dimethoxycyclohexa-2,5-dien-1-one 
• 1381862-02-7 N-acetyl-3-chloro-p-benzoquinone imine dimethyl acetal 
• 33234-37-6 6-amino-2-chloro-3-methoxy-benzoic acid 
• 85778-01-4 6-chloro-5-methoxy-isatin 
• 38608-06-9 5-chloro-4-methoxy-o-phenylenediamine 
• 1026083-32-8 1-Azido-5-chloro-4-methoxy-2-nitro-benzene 
• 160088-54-0 5-Chloro-4-methoxy-2-nitroaniline 
• 220587-30-4 N-acetyl-3-chloro-4-tetrahydropyranyloxy-aniline 
• 174668-87-2 3-chloro-4-tetrahydropyranyloxy-aniline 
• 160088-53-9 N-(5-chloro-4-methoxy-2-nitrophenyl)-acetamide 
• 130420-87-0 hydroxyimino-acetic acid-(3-chloro-4-methoxy-anilide) 

Relevant academic research and scientific papers

General rhodium-catalyzed oxidative cross-coupling reactions between anilines: Synthesis of unsymmetrical 2,2′-diaminobiaryls

Described herein is a dual chelation-assisted RhCl3-catalyzed oxidative C-H/C-H cross-coupling reaction of aniline derivatives. The highlight of this methodology is the chemo- and regioselective cross-coupling between electronically similar substrates, which represents a highly challenging task in oxidative Ar-H/Ar-H cross-coupling reactions. Furthermore, this Cp?-free catalytic reaction tolerates a range of functional groups and requires only a low molar ratio of coupling partners. These features expedite the synthesis of unsymmetrical 2,2′-diaminobiaryls.

Selective Csp2-Csp bond cleavage: The nitrogenation of alkynes to amides

Breakthrough: A novel catalyzed direct highly selective C sp 2-C sp bond functionalization of alkynes to amides has been developed. Nitrogenation is achieved by the highly selective C sp 2-Csp bond cleavage of aryl-substituted alkynes. The oxidant-free and mild conditions and wide substrate scope make this method very practical. Copyright

PHOSPHOGLYCERATE KINASE INHIBITORS

Disclosed are compounds of formula (I) or pharmaceutical acceptable salts thereof, wherein R1, R2, R3 and R4 are as defined in the description. Disclosed are also the methods of making said compounds, and compositions containing said compounds which are useful for inhibiting kinases such as phosphoglycerate kinase.

Palladium-catalyzed C-H aminations of anilides with N - fluorobenzenesulfonimide

The first amide-directed, palladium-catalyzed, intermolecular, highly selective C-H aminations with the non-nitrene-based nitrogen source N-fluorobenzenesulfonimide have been developed. This methodology might provide a new pathway for directed metal-catalyzed aromatic C-H amination.

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.

Positive allosteric modulators of the nicotinic acetylcholine receptor

The invention provides compounds of Formula I: These compounds may be in the form of pharmaceutical salts or compositions, may be in pure enantiomeric form or racemic mixtures, and are useful in pharmaceuticals used to treat diseases or conditions in which α7 nAChR is known to be involved.

NON-PEPTIDE GNRH AGENTS, PHARMACEUTICAL COMPOSITIONS AND METHODS FOR THEIR USE

Non-peptide GnRH agents capable of inhibiting the effect of gonadotropin-releasing hormone are described. Such compounds and their pharmaceutically acceptable salts, prodrugs, and active metabolites are suitable for treating mammalian reproductive disorders and steroid hormone-dependent tumors as well as for regulating fertility, where suppression o￡ gonadotropin release is indicated. Methods for synthesizing the compounds and intermediates useful in their preparation are also described.

Novel thiopyrano[3,2-b] and cycloalkeno[1,2-b]indole derivatives with high inhibitory properties in LTB4 production

Series of thiopyrano[3,2-b] and cycloalkeno[1,2-b]indoles were synthesized and evaluated in order to determine the necessary structural requirements for high leukotrienes biosynthesis inhibition. In vitro experiments showed that compounds 11b and 12b belonging to the second series were the most active and selective compounds on LTB4 production. Further in vivo investigations have shown additional very significant activity in the acute phorbol ester induced mouse ear swelling which is predictive of potential antipsoriatic properties.

Hypoxia-Selective Agents Derived from Quinoxaline 1,4-Di-N-oxides

Hypoxic cells, which are a common feature of solid tumors, but not normal tissues, are resistant to both anticancer drugs and radiation therapy.Thus the identification of drugs with selective toxicity toward hypoxic cells is an important objective in anticancer chemotherapy.The benzotriazine di-N-oxide (SR 4233, Tirapazamine) has been shown to be an efficient and selective cytotoxin for hypoxic cells.Since the bioreductive activation of Tirapazamine is thought to be due to the presence of the 1,4-di-N-oxide moiety, a series of 3-aminoquinoxaline-2-carbonitrile 1,4-di-N-oxides with a range of electron-donating and -withdrawing substituents in the 6- and /or 7- positions has been synthesized and evaluated for toxicity to hypoxic cells.Electrochemical studies of the quinoxaline di-N-oxides and Tirapazamine showed that as the electron-withdrawing nature of the 6(7)-substituent increases, the reduction potential becomes more positive and the compound is more readily reduced.Apart from the unsubstituted 6a and the 6,7-dimethyl derivative 6c, the quinoxaline di-N-oxide have reduction potentials significantly more positive than Tirapazamine (Epc -0.90 V).The most potent cytotoxins to cells in culture were the 6,7-dichloro and 6,7-difluoro derivatives 6i and 6l, which were 30-fold more potent than Tirapazamine.The 6(7)-fluoro and 6(7)-chloro compounds, 6e and 6h, showed the greatest hypoxia selectivity.Four of the compounds, 6e, 6f, 6h and 6i, killed the inner cells of multicellular tumor spheroids in vitro.In vivo Balb/c mice tolerated a dose of these four compounds twice the size of that of Tirapazamine.This study demonstrates that quinoxaline 1,4-di-N-oxides could provide useful hypoxia-selective therapeutic agents.

Polyaza Heterocycles. Part 2. Nucleophilic Substitution of Halogens in Halogenoquinoxalinocinnolines

10-Chloroquinoxalinocinnoline readily undergoes methoxydechlorination when treated with sodium methoxide.The 1-, 2-, 3-, 4- and 9-chloro isomers are unreactive towards this reagent, but the 9,10-dichloro derivative undergoes substitution of both chlorines (the 10-position being much the more reactive).The 9- and 10-bromo analogues are both unreactive towards sodium methoxide, but the 9- and 10-fluoro analogues are both highly reactive, to the extent that it has not been possible even to isolate the 10-fluoro compound.Routes to 9- and 10-piperidinoquinoxalinocinnolines are described.