5470-75-7

Usage

Uses

Used in Pharmaceutical Industry:
6-chloroquinolin-8-amine is used as a chemical intermediate for the synthesis of fungitoxic analogs, which are essential in developing antifungal medications. These analogs target and inhibit the growth of fungi, providing a treatment option for various fungal infections.
Used in Chemical Synthesis:
In the field of chemical synthesis, 6-chloroquinolin-8-amine serves as a key building block for creating more complex molecules with potential applications in different industries, such as agriculture, pharmaceuticals, and materials science. Its unique structure allows for further functionalization and modification to develop novel compounds with desired properties.

InChI:InChI=1/C9H7ClN2/c10-7-4-6-2-1-3-12-9(6)8(11)5-7/h1-5H,11H2

Upstream product

• 68527-66-2 6-chloro-8-nitroquinoline 
• 7647-01-0 hydrogenchloride 
• 89-63-4 4-Chloro-2-nitroaniline 
• 612-57-7 6-chloroquinoline 

Downstream Products

• 4199-89-7 5-Chloro-1,10-phenanthroline 
• 703-66-2 6,8-Dichloroquinoline 
• 27318-90-7 1,10-phenanthroline-5,6-dione 

Relevant academic research and scientific papers

Merging Annulation with Ring Deconstruction: Synthesis of (E)-3-(2-Acyl-1 H-benzo[ d]imidazol-4-yl)acrylaldehyde Derivatives via I2/FeCl3-Promoted Dual C(sp3)-H Amination/C-N Bond Cleavage

An unprecedented I2/FeCl3-promoted cascade reaction of aryl methyl ketones with 8-aminoquinolines for the convenient synthesis of (E)-3-(2-acyl-1H-benzo[d]imidazol-4-yl)acrylaldehydes was developed by merging annulation with ring deconstruction. This novel strategy unlocked the new reactivity of 8-aminoquinolines and provided an attractive platform for the ring opening of unactivated N-heteroaromatic compounds. Preliminary mechanistic investigation suggested that dual C(sp3)-H amination/C-N bond cleavage were key reaction steps. Furthermore, late-stage modification of the obtained products successfully delivered pyrazole and isoxazole derivatives, increasing the practicability and application potential of this methodology in organic synthesis.

Visible Light-Promoted Photocatalytic C-5 Carboxylation of 8-Aminoquinoline Amides and Sulfonamides via a Single Electron Transfer Pathway

An efficient photocatalytic method was developed for the remote C5-H bond carboxylation of 8-aminoquinoline amide and sulfonamide derivatives. This methodology uses in situ generated ?CBr3 radical as a carboxylation agent with alcohol and is further extended to a variety of arenes and heteroarenes to synthesize the desired carboxylated product in moderate-to-good yields. The reaction proceeding through a single electron transfer pathway was established by a control experiment, and a butylated hydroxytoluene-trapped aryl radical cation intermediate in high-resolution mass spectrometry was identified.

Novel small molecules with selective cytotoxicity against human microvascular endothelial cell proliferation

Disclosed herein are angiogenesis inhibitors represented by formula (I) or formula (II): The variables for formulas (I) and (II) are defined herein.

Piperazine-piperidine antagonists and agonists of the 5-HT1A receptor

The present invention relates to novel piperazine-piperidine compounds. The compounds are useful as 5-HT1A binding agents, particularly as 5-HT1A receptor antagonists and agonists. These compounds are useful in treating central nervous system disorders, such as cognition disorders, anxiety disorders, depression and sexual dysfunction.

ARYLPIPERAZINYL-CYCLOHEXYL INDOLE DERIVATIVES FOR THE TREATMENT OF DEPRESSION

Compounds are provided which are useful for the treatment of serotonin-affected neurological disorders which comprise (I) wherein: Ra, R1, R2 and R3 are each, independently, hydrogen, or a substituent selected from halogen, CF3, alkyl, alkoxy, MeSO2, amino or aminocarbonyl (each optionally substituted by one or two groups selected from alkyl and benzyl) carboxy, or alkoxycarbonyl; or two adjacent of Ra and R1-4 together can form a 5-7 membered carbocyclic or heterocyclic ring which is optionally substituted by a substituent defined above; R4 is hydrogen, halogen, or alkyl; R5 is hydrogen, alkyl, arylalkyl, or aryl; R6 is hydrogen, halogen, CF3, CN, carbamide, alkoxy or benzyloxy; X1, X2 and X3 are each carbon or one of X1, X2 or X3 may be nitrogen; Y is CH or nitrogen; and Z is carbon or nitrogen; or pharmaceutically acceptable salts thereof.

Aryl-8-azabicyclo [3.2.1] octanes for the treatment of depression

The present invention includes compounds of formula I wherein A, X, n, Ar1, and Ar2 are defined as set forth herein. These compounds may be used to treat depression. The invention also includes formulations containing these compounds, and methods for making and using compounds of this invention.

Preparation and Fungitoxicity of 3,6-Dichloro- and 3,6-Dibromo-8-Quinolinols

3,6-Dichloro- and 3,6-dibromo-8-quinolinols were prepared by direct halogenation of 8-nitroquinoline by N-halosuccinimide in acetic acid or by halogenation of the corresponding 6-halo-8-nitroquinoline prepared via a Skraup reaction.The nitro group was reduced to amino and the amine was hydrolyzed to the phenol in 70percent sulfuric acid at 220 deg C.The fungitoxicity of 3,6-dichloro- and 3,6-dibromo-8-quinolinols, as well as intermediates in their preparation, against Aspergillus niger, Aspergillus oryzae, Myrothecium verrucaria, Trichoderma viride, and Mucor cirinelloides was determined. 3,6-dichloro-8-quinolinol is the most fungitoxic analogue of this class of compounds observed to date. - Keywords. 3,6-dichloro-8-nitroquinoline; 3,6-dibromo-8-nitroquinoline; 8-amino-3,6-dichloroquinoline; 8-amino-3,6-dibromoquinoline; 3,6-dichloro-8-quinolinol; 3,6-dibromo-8-quinolinol; 1H NMR spectra.

Electron Transfer and Ion Pairing, 27. Preparation of Semiquinone Ion Pairs by Reduction of Quinones Using Tetraalkylammonium Boranate in Aprotic Salt Solutions: 1,10-Phenanthrolin-5,6-dione

Ion pairs of 1,10-phenanthrolin-5,6-dione radical anion -Me+n>*+(n-1) with Me+n = Mg2+, Ca2+, Sr2+, Zn2+, Cd2+, Pb2+ and La3+ are advantageously prepared in aprotic DMF solution containing appropriate metal salts Me+nX- by using the "mild" single-electron reducing agent tetra(n-butyl)ammonium-boranate R4N+BH4-.For comparison, the "nacked" radical anion with the largely interaction-free + counter cation is chosen, which is formed on reduction with potassium in THF solution of (2.2.2)-cryptand.Addition of excess Na+- to the reduction solution only yields a solvent-separated ion pair M*-)DMF...(Na+)DMF, whereas in the presence of multiply charged counter cations Me+n the respective contact ion pair radical cations -Me+n>*+(n-1) are formed.Their g values decrease with increasing nuclear charge of Me+n and their metal-s-spin densities increase with the effective counter cation charge n+/rMe+n.The ESR/ENDOR data recorded suggest Me+n complexation by the δ-OC-COδ- chelate tongs and the ion pair stability, which is modified by the dielectric properties of the solvent used, may be rationalized by the Coulombic attraction between the radical anion M*- and the counter cations Me+n.Keywords: 1,10-Phenanthrolin-5,6-dione, Reduction by R4N+BH4-, Contact Ion Pairs, ESR/ENDOR Spectra