- Preparation method of 2- novel chloronicotinic acid (by machine translation)
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The method disclosed by the invention 2 - comprises the following steps: reacting the obtained :1) product with trichlorooxygen phosphorus, in the presence of 1) an acid, to give 2 - the product of 2 - the present invention ;2) in the following steps: reacting the obtained product with phosphorus oxychloride, in 2 - the presence of a ;3) base with 2) phosphorus oxychloride in the presence of a base, 2 - 2 . (by machine translation)
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Paragraph 0041-0044
(2020/02/14)
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- Visible-light-driven catalytic oxidation of aldehydes and alcohols to nitriles by 4-acetamido-tempo using ammonium carbamate as a nitrogen source
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A mild and efficient route to prepare nitriles from aldehydes by combining photoredox catalysis with oxoammonium cations is reported. The reaction is performed using ammonium carbamate as the nitrogen source. The practicality of the method is increased by the extension of the dual catalytic system to one-pot two-step conversion of alcohols to nitriles.
- Nandi, Jyoti,Leadbeater, Nicholas E.
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supporting information
p. 9182 - 9186
(2019/11/05)
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- Environment-friendly preparation method of 2-chloro-3-cyanopyridine
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The invention discloses an environment-friendly preparation method of 2-chloro-3-cyanopyridine. The method comprises the steps of dissolving 3-cyanopyridine N-oxide as a raw material into a certain amount of an organic solvent, adding an additive, organic alkali and a phase transfer catalyst to form a raw material system, controlling to form a proper temperature, dissolving bis(trichloromethyl)carbonate in a certain amount of the organic solvent to obtain a mixture, slowly dropwise adding the mixture into the raw material system for reaction, and after the reaction is finished, carrying out simple treatment, so as to obtain 2-chloro-3-cyanopyridine. The preparation method is simple, the reaction period is short, a phosphorus-containing reagent is replaced with an environment-friendly chlorination reagent, and heavy metals are not adopted; and compared with the prior art, the method has the advantages that the environmental pollution is low, the operation is safe, the cost is low, and the preparation method is suitable for industrial production. The method is applied to the environment-friendly chlorination reaction of 3-cyanopyridine N-oxide and is not limited to the preparation of2-chloro-3-cyanopyridine.
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Paragraph 0021-0064
(2019/03/08)
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- 2-chloro-3-cyanopyridine preparation process
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The invention provides a 2-chloro-3-cyanopyridine preparation process which includes the steps: dissolving N-oxynicotinamide in an organic solvent; dripping phosphorus oxychloride at the temperature of 15+/-5 DEG C; dripping organic alkali at the temperature of 10+/-5 DEG C after dripping; keeping the temperature of 10+/-5 DEG C to stir mixture for 30+/-10 minutes after dripping; heating the mixture to reach the temperature of 35+/-10 DEG C, and keeping the temperature for 1+/-0.5 hour; heating the mixture to reach the temperature of 55+/-5 DEG C, and keeping the temperature for 1+/-0.5 hour;heating the mixture to reach the temperature of 95-100 DEG C, and keeping the temperature for 4+/-1 hours to obtain chloride reaction solution after temperature keeping; performing reduced pressure distillation on the chloride reaction solution until flow out of visible liquid is omitted; adding water, controlling the temperature to reach 65+/-5 DEG C, and stirring mixture for 2+/-0.5 hour; cooling the mixture to reach the temperature of 20+/-5 DEG C, stirring the mixture for 30+/-10 minutes, and filtering the mixture to obtain a wet 2-chlorine-3-cyanopyridine product. According to the process, two mixed organic alkali substances serve as catalysts, and the yield of 2-chlorine-3-cyanopyridine is improved to some extent.
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Paragraph 0016-0021; 0023; 0025
(2019/04/04)
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- Combining Oxoammonium Cation Mediated Oxidation and Photoredox Catalysis for the Conversion of Aldehydes into Nitriles
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A method to oxidize aromatic aldehydes to nitriles has been developed. It involves a dual catalytic system of 4-acetamido-TEMPO and visible-light photoredox catalysis. The reaction is performed using ammonium persulfate as both the terminal oxidant and nitrogen source.
- Nandi, Jyoti,Witko, Mason L.,Leadbeater, Nicholas E.
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supporting information
p. 2185 - 2190
(2018/09/29)
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- A halogenated nitrogen-containing unsaturated cyclic hydrocarbon preparation method
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The invention discloses a halogenated nitrogen-containing unsaturated cyclic hydrocarbon of the preparation method, the steps of: (1) the nitrogen-containing unsaturated cyclic hydrocarbon dissolved in hydrochloric acid or hydrobromic acid, addition of an oxidizing agent, the reaction system halogenated reaction, in the reaction process timing sampling detection, when detecting the target product quality of a halide accounted for is a reaction system in the total of the organic matter of 70% - 95% when, added to the reaction system in the terminator to terminate reaction, to obtain containing nitrogen-containing unsaturated cyclic hydrocarbon feed; (2) to the liquid mixed into the organic solvent extraction, extraction to obtain the organic phase, the organic phase temperature is reduced to make the solid precipitation or distilling the organic solvent to obtain a liquid product to be deducted, the resulting solid or liquid product is halogenated nitrogen-containing unsaturated cyclic hydrocarbon. The method solves the problem of the nitrogen-containing unsaturated cyclic hydrocarbon over [...] reaction problems.
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Paragraph 0020
(2018/05/16)
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- PhPOCl2as a potent catalyst for chlorination reaction of phenols with PCl5
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Phenols are easily converted to the corresponding aryl chlorides by using phosphorus pentachloride (PCl5) and a catalytic amount of phenylphosphonic dichloride (PhPOCl2), which is a new efficient method for synthesis of aryl chloride in good yields.
- Wu, Jiang,Zhou, Junpeng,Shi, Yalei,Zhu, Jintao
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supporting information
p. 1619 - 1624
(2016/10/09)
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- A continuous reaction to produce 2-chloro-3-cyano pyridine method
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The invention belongs to the field of organic synthesis, and particularly relates to a method for producing 2-chloro-3-cyanopyridine. The method is implemented by taking nicotinonitrile-1-oxide, phosphorus oxychloride and triethylamine as raw materials through the steps that the three raw materials are simultaneously continuously dropwise added into a first reactor, and the reaction temperature is controlled at minus 10-40 DEG C; and a reaction liquid in the first reactor continuously enters subsequent reactors connected in series to react at a reaction temperature of 80-100 DEG C, 1-2 hours later, the reaction liquid is distilled for recovering phosphorus oxychloride, and the phosphorus oxychloride is subjected to hydraulic analysis, so that 2-chloro-3-cyanopyridine is obtained. The method is implemented by adopting a continuous reaction thought, and reaction conditions in the related reactors are smooth, so that the implementation of automation control is facilitated, therefore, the method has the advantages of safe process, high production efficiency, stable product quality, and the like.
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Paragraph 0013; 0014; 0015; 0016
(2016/10/07)
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- Application of 1,1-ADEQUATE, HMBC, and Density Functional Theory to Determine Regioselectivity in the Halogenation of Pyridine N-Oxides
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The 1,1-ADEQUATE spectrum clearly shows specific two-bond proton to carbon correlations to unequivocally distinguish the major and minor regioisomers of ortho-halogenated pyridines and to aid in assignment of the corresponding proton and carbon chemical shifts. M06-2X/6-31+G(d,p) free energies of the regioisomeric intermediates arising from deprotonation correctly predict the experimentally observed preference and thus can be used to tune the substituent pattern to yield a desired regiochemical outcome.
- Hwang, Tsang-Lin,Bartberger, Michael D.,Chen, Ying
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p. 1956 - 1959
(2016/06/01)
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- Highly Regioselective Halogenation of Pyridine N -Oxide: Practical Access to 2-Halo-Substituted Pyridines
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A highly efficient and regioselective halogenation reaction of unsymmetrical pyridine N-oxide under mild conditions is described. The methodology provides a practical access to various 2-halo-substituted pyridines, which are pharmaceutically important intermediates.
- Chen, Ying,Huang, Jinkun,Hwang, Tsang-Lin,Chen, Maosheng J.,Tedrow, Jason S.,Farrell, Robert P.,Bio, Matthew M.,Cui, Sheng
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supporting information
p. 2948 - 2951
(2015/06/30)
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- Straightforward access to ethyl 3-aminofuropyridine-2-carboxylates from 1-chloro-2-cyano- or 1-hydroxy-2-cyano-substituted pyridines
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The conditions of the synthesis of the four regioisomers of ethyl 3-aminofuropyridine-2-carboxylate are described and discussed in detail. The starting materials are either 1-chloro-2-cyanopyridines or 1-cyano-2- hydroxypyridines. Georg Thieme Verlag Stuttgart.
- Cailly, Thomas,Lemaitre, Stephane,Fabis, Frederic,Rault, Sylvain
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p. 3247 - 3251
(2008/04/03)
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- Synthesis of ortho-substituted cyanopyridines through lithio intermediate trapping
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Ortholithiation of 4-cyanopyridine using 2,2,6,6-tetramethylpiperidide (LiTMP) and trapping the lithio intermediate with electrophiles represents an efficient and straightforward access to ortho-substituted-4-cyanopyridines. The cyano group can be used as an ortho-directing group and allows the preparation of 3-halogeno-4-cyanopyridines. Reactivity of 2- and 3-cyanopyridines is also investigated and seems to give similar results.
- Cailly, Thomas,Fabis, Frédéric,Lema?tre, Stéphane,Bouillon, Alexandre,Rault, Sylvain
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p. 135 - 137
(2007/10/03)
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- Preparation of highly functionalized pyridylmagnesium reagents for the synthesis of polyfunctional pyridines
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Functionalized iodopyridines bearing either a chloride, ester or nitrile function were converted to the corresponding organomagnesium derivatives at -40°C or -78°C by treatment with i-PrMgBr (1.1 equiv, 0.5 h, > 90% yield). The resulting functionalized Grignard reagents react with aldehydes, TosCN directly or with allylic bromides and benzoyl chloride after transmetalation with CuCN leading to polyfunctional pyridines.
- Bérillon, Laurent,Leprêtre, Anne,Turck, Alain,Plé, Nelly,Quéguiner, Guy,Cahiez, Gérard,Knochel, Paul
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p. 1359 - 1360
(2007/10/03)
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- Process for the preparation of 2-halogeno-5-cyano pyridines
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The title compounds of the formula STR1 can be prepared by reacting methylene-glutaconic acid dinitriles of the formula with hydrogen halide of the formula In these formulae, X denotes fluorine, chlorine, bromine or iodine and R1 denotes --OR2 or --N(R2, R3), in which R2 and R3, independently of one another, represent straight-chain or branched C1 -C8 -alkyl, C3 -C8 -alkenyl, C2 -C8 -alkoxyalkyl, C4 -C8 -alkoxyalkenyl, C3 -C8 -cycloalkyl, C6 -C12 -aryl, C7 -C10 -aralkyl or a 5- to 8-membered saturated or unsaturated heterocyclic ring containing 1 or 2 heteroatoms from the group comprising N, O and S, where R2 and R3, with the N atom on which they are substituents, may also form a 5- to 8-membered ring which may contain a further heteroatom from the group comprising N, O and S.
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- Preparation of substituted 2-chloropyridines
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A process for the preparation of a substituted 2-chloropyridine derivatives of the formula STR1 in which R1, R2, R3 and R4 represent hydrogen or various other radicals, which comprises reacting a pyridine-1-oxide of the formula STR2 with an aromatic carbonyl chloride in the presence of an inert organic solvent and in the presence of an acid acceptor at a temperature between about -20° C. and 200° C.
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- Process for the preparation of substituted 2-chloropyridines
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A new process has been found for the preparation of substituted 2-chloropyridine derivatives of the formula (I) STR1 wherein R1 to R4 have the meanings as defined in the description. The new process is characterized in that pyridine 1-oxides of the formula II STR2 are reacted with a chlorine-containing phosphoric acid derivative from the series of the chlorophosphoric esters and chlorophosphoramides in the presence of an inert organic solvent and in the presence of an acid acceptor at temperatures between -20° C. and 200° C., and the resulting product is separated further, if appropriate. Compound (I) is known as an intermediate product for medicaments (cf.DE-A 2,812,585) or for insecticidel nitromethylene derivatives (cf. EP-A 163,855).
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- Site-Selectivity in the Reaction of 3-Substituted Pyridine 1-Oxides with Phosphoryl Chloride
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Site-selectivity in the reaction of 3-substituted pyridine 1-oxide with phosphoryl chloride was investigated.When a strongly electron-withdrawing group (e.g.CN, CONRR', COOR, or NO2) was substituted at the 3-position, the reaction of 3-substituted pyridine 1-oxides with phosphoryl chloride yielded 3-substituted 2-chloropyridines as the main products.Keywords- site-selectivity; 3-substituted pyridine 1-oxide; phosphoryl chloride; 3-substituted 2-chloropyridine; chlorination
- Yamanaka, Hiroshi,Araki, Tomio,Sakamoto, Takao
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p. 2244 - 2247
(2007/10/02)
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