2343-25-1

Usage

Uses

Used in Research and Development:
2-AMINO-5-FLUOROACETOPHENONE is used as a research chemical for the development of new organic and pharmaceutical compounds. Its unique structure makes it a versatile building block in the synthesis of various molecules with potential applications in different fields.
Used in Organic Synthesis:
2-AMINO-5-FLUOROACETOPHENONE is used as an organic synthesis intermediate, playing a crucial role in the production of a wide range of organic compounds. Its reactivity and functional groups allow for various chemical reactions, leading to the formation of diverse molecules with specific properties and applications.
Used in Pharmaceutical Industry:
2-AMINO-5-FLUOROACETOPHENONE is used as a pharmaceutical intermediate, contributing to the development of new drugs and therapeutic agents. Its unique structure and reactivity make it an essential component in the synthesis of various pharmaceutical compounds, potentially leading to the discovery of novel treatments for various diseases and conditions.

Synthesis

600 g of 2-ethynyl-4-fluoroaniline and 4 L of water were added to the reaction flask, and then 476 g of hydrochloric acid (concentration: 35%) was added, and thereaction was carried out at 50 °C for 36 hours.After the reaction, the temperature is lowered to 20-25 °C, the reaction solution is adjusted to pH 8-9 with 50% sodium hydroxide solution, thetemperature is controlled to not exceed 30 °C during pH adjustment, and the filter cake is washed with 1 L of water and decompressed at 50 °C. After drying for 12 h, 622 g of pale yellow solid was obtained, yield91.4%.HPLC purity was 99.2%.

InChI:InChI=1/C8H8FNO/c1-5(11)7-4-6(9)2-3-8(7)10/h2-4H,10H2,1H3

Upstream product

• 61272-77-3 2-cyano-4-fluoroaniline 
• 887903-03-9 4-fluoro-2-ethynylaniline 
• 676-58-4 methylmagnesium chloride 
• 75-05-8 acetonitrile 
• 371-40-4 4-fluoroaniline 
• 446-08-2 2-amino-5-fluorobenzoic acid 
• 917-54-4 methyllithium 
• 75-16-1 methylmagnesium bromide 
• 351-83-7 4'-fluoroacetanilide 

Downstream Products

• 1417901-30-4 1-((5-fluoro-2-(phenylamino))phenyl)ethanone 
• 5273-41-6 4-fluoro-2-(prop-1-en-2-yl)aniline 

Relevant academic research and scientific papers

Catalytic Asymmetric Addition of Diorganozinc Reagents to Pyrazole-4,5-Diones and Indoline-2,3-Diones

The catalytic enantioselective diorganozinc additions to cyclic diketones including pyrazolin-4,5-diones and isatins have been developed. In the presence of morpholine-containing chiral amino alcohol ligand, the corresponding chiral cyclic tertiary alcohols were produced in good to excellent yields (up to 97 %) and enantioselectivities (up to 95 % ee). The notable feature of this protocol includes its mild reaction conditions, Lewis acid additives free and broad functional group tolerance.

Experimental and Computational Studies on Cp*CyRh(III)/KOPiv-Catalyzed Intramolecular Dehydrogenative Cross-Couplings for Building Eight-Membered Sultam/Lactam Frameworks

Described herein is an unusual Cp*CyRh(III)-catalyzed intramolecular site-specific aryl C-H annulation, a highly chemoselective protocol providing direct access to eight-membered sultams/lactams with broad substrate/functional group tolerance. Experimental and computational studies reveal that such a transformation involves a unique PivOH-assisted aryl C-H activation/alkene insertion/β-H elimination/hydrogen-transfer process involving the Rh(III)-hydride species as the active intermediate with the concomitant release of H2 as the major byproduct, thus enabling the developed Cp*CyRh(III) catalysis with redox-neutral and highly atom-economical features.

Preparation method of lorlatinib intermediate compound

The invention relates to a preparation method of a lorlatinib intermediate compound. 4-fluoroacetanilide is taken as a raw material and carry out visible light Fries rearrangement in the presence of avisible light catalyst and visible light to obtain an i

Method for preparing 2-amino-5-fluoroacetophenone

The invention discloses a method for preparing 2-amino-5-fluoroacetophenone. The method comprises the following steps: under a heating condition, enabling 2-acetenyl-4-fluorophenylamine to react withan acid in water, and after the reaction is completed, p

Chemoselective Alkylation of Aminoacetophenones with Alcohols by Using a Palladacycle-Phosphine Catalyst

The development of efficient and environmentally benign palladacycle-phosphine catalyzed process to enable the formation of chemoselective C-alkylated or N-alkylated aminoacetophenones with alcohols is described. This methodology proved to be tunable by variation of the base and the temperature, which allows for the isolation of structurally diverse C-alkylated and N-alkylated aminoacetophenones. Moreover, this methodology has been applied to the synthesis of biologically and industrially important donepezil.

Water-Soluble Hypervalent Iodine(III) Having an I-N Bond. A Reagent for the Synthesis of Indoles

A readily accessible and bench-stable water-soluble hypervalent iodine(III) reagent (phenyliodonio)sulfamate (PISA) with an I-N bond was synthesized, and its structure was characterized by X-ray crystallography. With PISA, various indoles were synthesized via C-H amination of 2-alkenylanilines involving an aryl migration/intramolecular cyclization cascade with excellent regioselectivity in aqueous CH3CN. Notably, using this new method as the key step, not only two drug molecules, indometacin and zidometacin, but also another bioactive molecule, pravadoline, were synthesized.

Catalyst-free geminal aminofluorination of ortho-sulfonamide-tethered alkylidenecyclopropanes via a Wagner-Meerwein rearrangement

A catalyst-free intramolecular geminal aminofluorination of ortho-sulfonamide-tethered alkylidenecyclopropanes has been developed. The reaction proceeded through two SET processes with Selectfluor to give a fluorinated cyclopropylcarbinyl cation and a further Wagner-Meerwein rearrangement to generate a cyclobutyl carbocation, which undergoes intramolecular nucleophilic capture by amide to forge fluorinated cyclobuta[b]indoline derivatives. A polycyclic multi-fluorinated byproduct was also formed through a Ritter-type reaction in some cases.

Selenium-promoted intramolecular oxidative amidation of 2-(arylamino)acetophenones for the synthesis of N-arylisatins

A convenient method for the synthesis of N-arylisatins from 2-(arylamino)acetophenones by using SeO2 as an oxidant is described. Various substituted N-arylisatins were selectively obtained in good to excellent yields. The reaction tolerates a wide range of functionalities. Copyright

Br?nsted acid/rhodium(II) cooperative catalytic asymmetric three-component aldol-type reaction for the synthesis of 3-amino oxindoles

Cooperation is key! Chiral Br?nsted acid/rhodium(II) cooperative catalysis enabled an enantioselective three-component aldol-type reaction of 3-diazo oxindoles and anilines with glyoxylates to give highly functionalized and structurally diverse 3-amino oxindoles in high stereoselectivity (>20:1 d.r., 99 % ee; see scheme). Copyright

QUINAZOLINE DERIVATIVES AS PDE10A ENZYME INHIBITORS

This invention is directed to compounds, which are PDE10A enzyme inhibitors. The invention provides a pharmaceutical composition comprising a therapeutically effective amount of a compound of the invention and a pharmaceutically acceptable carrier. The pr