Quinoline
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Quinoline
Quinoline is a heterocyclic aromatic organic compound with the chemical formula C9H7N. It is a colorless hygroscopic liquid with a strong odor. Aged samples, especially if exposed to light, become yellow and later brown. Quinoline is only slightly soluble in cold water but dissolves readily in hot water and most organic solvents. Quinoline itself has few applications, but many of its derivatives are useful in diverse applications. A prominent example is quinine, an alkaloid found in plants. Over 200 biologically active quinoline and quinazoline alkaloids are identified. 4-Hydroxy-2-alkylquinolines (HAQs) are involved in antibiotic resistance. Occurrence and isolation Quinoline was first extracted from coal tar in 1834 by German chemist Friedlieb Ferdinand Runge; he called quinoline ''leukol'' ("white oil" in Greek). Coal tar remains the principal source of commercial quinoline. In 1842, French chemist Charles Gerhardt obtained a compound by dry distilling quinine, stry ...
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Quinoline From Aniline
Quinoline is a heterocyclic aromatic organic compound with the chemical formula C9H7N. It is a colorless hygroscopic liquid with a strong odor. Aged samples, especially if exposed to light, become yellow and later brown. Quinoline is only slightly soluble in cold water but dissolves readily in hot water and most organic solvents. Quinoline itself has few applications, but many of its derivatives are useful in diverse applications. A prominent example is quinine, an alkaloid found in plants. Over 200 biologically active quinoline and quinazoline alkaloids are identified. 4-Hydroxy-2-alkylquinolines (HAQs) are involved in antibiotic resistance. Occurrence and isolation Quinoline was first extracted from coal tar in 1834 by German chemist Friedlieb Ferdinand Runge; he called quinoline ''leukol'' ("white oil" in Greek). Coal tar remains the principal source of commercial quinoline. In 1842, French chemist Charles Frédéric Gerhardt, Charles Gerhardt obtained a compound by ...
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Combes Quinoline Synthesis
The Combes quinoline synthesis is a chemical reaction, which was first reported by Combes in 1888. It involves the condensation of unsubstituted anilines (1) with β-diketones (2) to form substituted quinolines (4) after an acid-catalyzed ring closure of an intermediate Schiff base (3). Further studies and reviews of the Combes quinoline synthesis and its variations have been published by Alyamkina ''et al''., Bergstrom and Franklin, Born, and Johnson and Mathews. The Combes quinoline synthesis is often used to prepare the 2,4-substituted quinoline backbone and is unique in that it uses a β-diketone substrate, which is different from other quinoline preparations, such as the Conrad-Limpach synthesis and the Doebner reaction. Mechanism The reaction mechanism undergoes three major steps, the first one being the protonation of the oxygen on the carbonyl in the β-diketone, which then undergoes a nucleophilic addition reaction with the aniline. An intramolecular proton trans ...
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Alkaloid
Alkaloids are a class of basic, naturally occurring organic compounds that contain at least one nitrogen atom. This group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of similar structure may also be termed alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and, more rarely, other elements such as chlorine, bromine, and phosphorus.Chemical Encyclopedia: alkaloids
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Alkaloids are produced by a large variety of organisms including , , Medicinal plant, plants, an ...
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Quinine
Quinine is a medication used to treat malaria and babesiosis. This includes the treatment of malaria due to ''Plasmodium falciparum'' that is resistant to chloroquine when artesunate is not available. While sometimes used for nocturnal leg cramps, quinine is not recommended for this purpose due to the risk of serious side effects. It can be taken by mouth or intravenously. Malaria resistance to quinine occurs in certain areas of the world. Quinine is also used as an ingredient in tonic water to impart a bitter taste. Common side effects include headache, ringing in the ears, vision issues, and sweating. More severe side effects include deafness, low blood platelets, and an irregular heartbeat. Use can make one more prone to sunburn. While it is unclear if use during pregnancy causes harm to the baby, treating malaria during pregnancy with quinine when appropriate is still recommended. Quinine is an alkaloid, a naturally occurring chemical compound. How it works as a medicin ...
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Cinchonine
Cinchonine is an alkaloid found in '' Cinchona officinalis''. It is used in asymmetric synthesis in organic chemistry. It is a stereoisomer and pseudo- enantiomer of cinchonidine. It is structurally similar to quinine, an antimalarial Antimalarial medications or simply antimalarials are a type of antiparasitic chemical agent, often naturally derived, that can be used to treat or to prevent malaria, in the latter case, most often aiming at two susceptible target groups, young ... drug. References Secondary alcohols Vinyl compounds Quinoline alkaloids Quinuclidine alkaloids {{alkaloid-stub ...
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Doebner Reaction
The Doebner reaction is the chemical reaction of an aniline with an aldehyde and pyruvic acid to form quinoline-4-carboxylic acids.Bergstrom, F. W. ''Chem. Rev.'' 1944, ''35'', 156. (Review) The reaction serves as an alternative to the Pfitzinger reaction.W. Pfitzinger: ''Chinolinderivate aus Isatinsäure.'' In: ''Journal für Praktische Chemie.'' Band 33, Nr. 1, 1886, S. 100, doi:10.1002/prac.18850330110.Oscar Doebner: ''Ueber α-Alkylcinchoninsäuren und α-Alkylchinoline.'' In: ''Justus Liebigs Annalen der Chemie.'' Band 242, Nr. 3, 1887, S. 265–388, doi:10.1002/jlac.18872420302. Reaction mechanism The reaction mechanism is not exactly known, two proposals are presented here. One possibility is at first an aldol condensation, starting from the enol form of the pyruvic acid (1) and the aldehyde, forming an ''β,γ''-unsaturated α-ketocarboxylic acid (2). This is followed by a Michael addition with aniline to form an aniline derivative (3). After a cyclization at the benze ...
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Charles Frédéric Gerhardt
Charles Frédéric Gerhardt (21 August 1816 – 19 August 1856) was a French chemist, born in Alsace and active in Paris, Montpellier, and his native Strasbourg. Biography He was born in Strasbourg, which is where he attended the gymnasium (an advanced academic secondary school). He then studied at the Karlsruhe Institute of Technology, where Friedrich Walchner's lectures first stimulated his interest in chemistry. Next he attended the school of commerce in Leipzig, where he studied chemistry under Otto Linné Erdmann, who further developed his interest into a passion for questions of speculative chemistry. Returning home in 1834, he entered his father's white lead factory, but soon found that business was not to his liking, and after a sharp disagreement with his father in his 20th year he enlisted in a cavalry regiment. In a few months military life became equally distasteful, and he purchased his discharge with the assistance of the German chemist Justus von Liebig. After a s ...
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Pyridine
Pyridine is a basic heterocyclic organic compound with the chemical formula . It is structurally related to benzene, with one methine group replaced by a nitrogen atom. It is a highly flammable, weakly alkaline, water-miscible liquid with a distinctive, unpleasant fish-like smell. Pyridine is colorless, but older or impure samples can appear yellow, due to the formation of extended, unsaturated polymeric chains, which show significant electrical conductivity. The pyridine ring occurs in many important compounds, including agrochemicals, pharmaceuticals, and vitamins. Historically, pyridine was produced from coal tar. As of 2016, it is synthesized on the scale of about 20,000 tons per year worldwide. Properties Physical properties The molecular electric dipole moment is 2.2 debyes. Pyridine is diamagnetic and has a diamagnetic susceptibility of −48.7 × 10−6 cm3·mol−1. The standard enthalpy of formation is 100.2 kJ·mol−1 in the liquid phase ...
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Royal Society Of Chemistry
The Royal Society of Chemistry (RSC) is a learned society (professional association) in the United Kingdom with the goal of "advancing the chemistry, chemical sciences". It was formed in 1980 from the amalgamation of the Chemical Society, the Royal Institute of Chemistry, the Faraday Society, and the Society for Analytical Chemistry with a new Royal Charter and the dual role of learned society and professional body. At its inception, the Society had a combined membership of 34,000 in the UK and a further 8,000 abroad. The headquarters of the Society are at Burlington House, Piccadilly, London. It also has offices in Thomas Graham House in Cambridge (named after Thomas Graham (chemist), Thomas Graham, the first president of the Chemical Society) where ''RSC Publishing'' is based. The Society has offices in the United States, on the campuses of The University of Pennsylvania and Drexel University, at the University City Science Center in Philadelphia, Pennsylvania, in both Beijing a ...
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Hydrodenitrification
Hydrodenitrogenation (HDN) is an industrial process for the removal of nitrogen from petroleum. Organonitrogen compounds, even though they occur at low levels, are undesirable because they cause poisoning of downstream catalysts. Furthermore, upon combustion, organonitrogen compounds generate NOx, a pollutant. HDN is effected as general hydroprocessing, which traditionally focuses on hydrodesulfurization (HDS) because sulfur compounds are even more problematic. To some extent, hydrodeoxygenation (HDO) is also effected. Typical organonitrogen compounds in petroleum include quinolines and porphyrins and their derivatives. The total nitrogen content is typically less than 1% and the targeted levels are in the ppm range. As described in organic geochemistry, organonitrogen compounds are derivatives or degradation products of the compounds in the living matter that comprised the precursor to fossil fuels. In HDN, the organonitrogen compounds are treated at high temperatures with h ...
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Diesel Fuel
Diesel fuel , also called diesel oil, is any liquid fuel specifically designed for use in a diesel engine, a type of internal combustion engine in which fuel ignition takes place without a spark as a result of compression of the inlet air and then injection of fuel. Therefore, diesel fuel needs good compression ignition characteristics. The most common type of diesel fuel is a specific fractional distillate of petroleum fuel oil, but alternatives that are not derived from petroleum, such as biodiesel, biomass to liquid (BTL) or gas to liquid (GTL) diesel are increasingly being developed and adopted. To distinguish these types, petroleum-derived diesel is sometimes called petrodiesel in some academic circles. In many countries, diesel fuel is standardised. For example, in the European Union, the standard for diesel fuel is EN 590. Diesel fuel has many colloquial names; most commonly, it is simply referred to as ''diesel''. In the United Kingdom, diesel fuel for on-road use is c ...
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Aniline
Aniline is an organic compound with the formula C6 H5 NH2. Consisting of a phenyl group attached to an amino group, aniline is the simplest aromatic amine In organic chemistry, an aromatic amine is an organic compound consisting of an aromatic ring attached to an amine. It is a broad class of compounds that encompasses aniline Aniline is an organic compound with the formula C6 H5 NH2. Consi .... It is an industrially significant Commodity chemicals, commodity chemical, as well as a versatile starting material for fine chemical synthesis. Its main use is in the manufacture of precursors to polyurethane, dyes, and other industrial chemicals. Like most volatile amines, it has the odor of rotten fish. It Combustion, ignites readily, burning with a smoky flame characteristic of aromatic compounds. It is toxic to humans. Relative to benzene, it is electron-rich. It thus participates more rapidly in electrophilic aromatic substitution reactions. Likewise, it is also prone ...
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