- Method of synthesizing 4-alkylamino pyridine in mild condition
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The invention discloses a method of synthesizing 4-alkylamino pyridine in a mild condition, and belongs to the technical field of organic synthesis. The method comprises performing a nucleophilic substitution reaction on 4-chloropyridine hydrochloride with alkyl amine in the presence of an inhibitor to prepare the 4-alkylamino pyridine, wherein the reaction temperature is in a range of 30-150 DEG C, the reaction time is in a range of 1-10 hours, the inhibitor is a fluoride salt, and the mass ratio of the inhibitor to the 4-chloropyridine hydrochloride is (0.1-1):1. In order to solve the problem of production safety hidden danger caused by a sharp rise of temperature in such kind of nucleophilic substitution reactions, the method provided by the invention introduces the inhibitor to control the reaction speed. With the addition of the inhibitor, the rise of the reaction temperature is effectively controlled, the reaction temperature and reaction speed are reduced to a controllable range, and thus the method provides possibility for safe production and is suitable for large-scale production. In addition, the synthetic reaction has only one step, the yield can reach 80%, and compared with the products of nucleophilic substitution reactions with no inhibitors, the product purity is increased and can reach 99% or more.
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Paragraph 0020
(2018/01/17)
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- Inductive effects through Alkyl Groups - How long is long enough?
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The influence of the length of alkyl substituents on various kinetic, thermodynamic, and spectroscopic properties of 4-(dialkylamino)pyridines has been determined by using a combination of experimental and theoretical methods. The chain-length dependence of these properties has subsequently been analyzed by using a quantitative model for through-bond inductive effects. Substituent effects of linear alkyl groups show a saturation effect beyond four carbon atoms for numerous properties of 4-(dialkylamino)pyridines as test substrates. These observations can be rationalized by using an increment-based method for the calculation of inductive substituent effects. Copyright
- Tandon, Raman,Nigst, Tobias A.,Zipse, Hendrik
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supporting information
p. 5423 - 5430
(2013/09/02)
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- Preparation of the isomeric azaindoline family by intramolecular carbolithiation
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An operationally convenient, one-pot, three-step sequence has been developed that provides access to 3-substituted 4-, 5-, 6-, and 7-azaindolines (2,3-dihydro-1H-pyrollopyridines) via intramolecular carbolithiation of the aryllithium derived from an appro
- Bailey, William F.,Salgaonkar, Paresh D.,Brubaker, Jason D.,Sharma, Vijayata
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supporting information; body text
p. 1071 - 1074
(2009/04/06)
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- Complex base-induced generation of 3,4-didehydropyridine derivatives: New access to aminopyridines or pyridones
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The complex base, NaNH2-tert-BuONa, in THF easily transforms 3-bromopyridine and 2-pyridone derivatives into the corresponding hetarynes. The reaction of representative amines (dialkylamines, morpholine, piperidine) with these reactive intermediates leads to the preparation of aminopyridines in good yields and illustrates the synthetic usefulness of such reactions.
- Vinter-Pasquier, Karine,Jamart-Gregoire, Brigitte,Caubere, Paul
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p. 2113 - 2129
(2007/10/03)
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