35975-00-9

Usage

Uses

Used in Pharmaceutical Industry:
5-Amino-6-nitroquinoline is used as a key intermediate for the synthesis of imidazoquinoline derivatives, which are important in the development of pharmaceutical compounds with potential therapeutic applications.
Used in Chemical Research:
5-Amino-6-nitroquinoline serves as a subject of study in various electrochemical reduction techniques, contributing to the understanding of its chemical behavior and potential applications in different fields, including the development of new materials and compounds.

InChI:InChI=1/C9H7N3O2/c10-9-6-2-1-5-11-7(6)3-4-8(9)12(13)14/h1-5H,10H2

Upstream product

• 613-50-3 6-nitroquinoline 
• 74-89-5 methylamine 
• 100-01-6 4-nitro-aniline 

Downstream Products

• 233-55-6 imidazo<4,5-f>quinoline 
• 93201-85-5 2-methyl-1(3)H-imidazo[4,5-f]quinoline 
• 42143-23-7 5,6-diaminoquinoline 
• 93201-92-4 2-(4-methoxyphenyl)-1H-imidazo[4,5-f]quinoline 
• 76180-96-6 2-Amino-3-methylimidazo[4,5-f]quinoline 

Relevant academic research and scientific papers

Vicarious nucleophilic amination of nitroquinolines by 1,1,1- trimethylhydrazinium iodide

(Chemical Equation Presented) The amination of 3-, 5-, 6-, 7- and 8-nitroquinoline via the vicarious nucleophilic substitution of hydrogen (VNS) with 1,1,1-trimethylhydrazinium iodide (TMHI) in the presence of t-BuOK in DMSO was studied. The amination occurs regioselectively giving ortho or ortho and para isomers relative to the nitro group with a high yield (95-86%). 2-Nitroquinoline does not undergo vicarious amination but displacement of the labile nitro group by an amino group occurs and then transformation to an imine compound and hydrolysis gives 2(1H)-quinolinone.

Vicarious nucleophilic amination of Nitroquinolines with 4-amino-1,2,4-triazole

3-, 5-. 6-, 7- and 8-Nitroquinolines react with 4-amino-l,2,4-triazole in basic medium (potassium tert-butoxide-dimethyl sulfoxide) giving amino products of the vicarious nucleophilic substitution (VNS) of hydrogen, predominantly at ortho position to the nitro group, except 8-nitroquinoline, which reacts at para position. Additionally, furazano[3,4-f]- and furazano[3,4-zh]quinoline were obtained in the case of 5- and 8- nitroquinoline, respectively. 2-Nitroquinoline was aminated to 2-quinolino(l,2,4-triazol-4-yl)amine in these conditions.

Nitroarylamines via the Vicarious Nucleophilic Substitution of Hydrogen: Amination, Alkylamination, and Arylamination of Nitroarenes with Sulfenamides

A new reaction of sulfenamides with electrophilic arenes under basic conditions is described. The σ adducts formed from nitroarenes and the anions of sulfenamides undergo elimination of thiol to produce the corresponding o- and/or p-nitroanilines. This reaction is analogous to the known alkylation and hydroxylation of nitroarenes via the vicarious nucleophilic substitution of hydrogen (VNS). The reaction gives access to a wide range of substituted nitroanilines, nitronaphthylamines, and aminoheterocycles. By means of the reaction with N-alkyl- and N-arylsulfenamides, it is possible to obtain N-alkylnitroanilines and nitrodiarylamines. By varying the structure of sulfenamide and the reaction conditions, particularly the nature and concentration of the base, it is possible to control the orientation of animation.

Oxidative Methylamination of Nitroquinolines

3-, 5-, 6-, 7- and 8-nitroquinoline as well as 5,7- and 6,8-dinitroquinoline are methylaminated with a liquid methylamine solution of potassium permanganate (LMA/PP) to the corresponding mono- and bis(methylamino)-substituted compounds. 2-Nitroquinoline is aminated with LMA/PP to 2-(methylamino)quinoline.The intermediate methylamino ?-adducts of 3-nitro- and 5,7- and 6,8-dinitroquinoline are detected by 1H-NMR spectroscopy.Quantum chemical calculations for the mononitroquinolines suggest that the experimentally observed regioselectivity of the methylamination is controlled by an interaction of frontal molecular orbitals (FMO) of the reagents. Key Words: Methylaminations / ?-Adducts, methylamino / Calculations, FMO / Quinolines / Aminations

SYNTHESIS AND BIOLOGICAL ACTIVITY OF 2-MERCAPTO-1H-IMIDAZOQUINOLINE DERIVATIVES

5,6-Diaminoquinoline (1c) which was prepared from 6-nitroquinoline (1a) by successive amination and reduction, upon condensation with carbondisulphide in alkaline medium yielded 2-mercapto-1H-imidazoquinoline (IIa).This on treatment with alkyl, aralkyl and acid halides gave the corresponding thioethers (II b-i) and thioesters (II j,k) respectively.Their structures were established by elemental analysis and spectral data (I.R., P.M.R., 13C N.M.R. and mass).The biological activity of some of the compounds was evaluated.

Frontier Orbital Interactions in the Regioselectivity of the Amination of Nitroquinolines by Liquid Ammonia/Potassium Permanganate

5-Nitro-,6-nitro-,7-nitro-,8-nitro-,and 2-nitroquinoline and 5,7-dinitro and 6,8-dinitroquinoline were aminated in a liquid ammonia solution of potassium permanganate. 8-Nitro and 2-nitroquinoline were found to be unreactive.The intermediary ?-adducts,formed between 5,7-dinitro- and 6,8-dinitroquinoline and liquid ammonia, could be detected by 1H NMR spectroscopy.FMO calculations nicely confirm the experimentally observed regioselectivity of the amination.

Condensed Heterocyclics: Part XV - Synthesis and Oxidation Reactions of 1,2,5-Thiadiazoloquinoline

1,2,5-Thiadiazoloquinoline (III) has been synthesised by the reaction of thionyl chloride with 5,6-diaminoquinoline.Its reactions have been studied and the various products isolated have been characterised by elemental analyses, IR and PMR data.