Chapter IX Aminopyridines (pages 1–177): Andrew S. Tomcufcik and Lee N. Starker
Chapter X Pyridinecarboxylic Acids (pages 179–346): Eugene P. Oliveto
Chapter XI Pyridine Side?Chain Carboxylic Acids (pages 347–507): John C. Godfrey
Chapter XII Pyridinols and Pyridones (pages 509–890): Herbert Meislich
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Court cases of the Intl Symposium on reliable country Chemistry in China, held August 9-12, 2002 in Changchun, China. contains the superb learn effects lately received by way of a large spectrum of reliable nation chemists either from China and from out of the country.
Content material: bankruptcy IX Aminopyridines (pages 1–177): Andrew S. Tomcufcik and Lee N. StarkerChapter X Pyridinecarboxylic Acids (pages 179–346): Eugene P. OlivetoChapter XI Pyridine aspect? Chain Carboxylic Acids (pages 347–507): John C. GodfreyChapter XII Pyridinols and Pyridones (pages 509–890): Herbert Meislich
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Additional resources for Chemistry of Heterocyclic Compounds: Pyridine and its Derivatives, Part Three, Volume 14
Aminopyridine are readily separated by steam distillation, the former compound being volatile while the latter is not (273). This technique is extremely useful in the separation of the isomers formed by nitration of 2-aminopyridines with both the 3 and 5 positions free. TVhen either position is occupied by a stable group, the nitro group enters the free position exclusively. T h e nitration of 2-acetamidopyridine gives 3- and 5-nitro-2aminopyridine. 2-Xitraminopyridine can also be isolated, indicating that deacylation occurs before nitration ( 2 3 4 ) .
A similar synthesis gives 1,4-dihy- (IX- 88) 57 Aminopyridines dro-4-imino-1-methylpyridine (445,446), which is also obtained by the action of methyl iodide upon 4-aminopyridine in the presence of sodium amide (446). 2-Aminopyridine is methylated on the amino group under these conditions (327). Similarly, the reaction of 4aminopyridine and 2,4-dinitrochlorobenzeneyields a quaternary salt, which by treatment with aqueous alkali is converted to the unstable I,4-dihydro-l-(2,4-dinitrophenyl)-4-iminopyridine (447,309).
In addition to alkylation, the secondary aminopyridines undergo the usual reactions of secondary amines, such as arylation and nitrosation. g. Diazotization Reactions 2-Amino- and 4-aminopyridines can be diazotized only in the presence of a strong acid. In weak acid, these amines apparently go directly to the hydroxy compound (33). Marckwald (41) diazotized 4-amino-2,6-lutidine in concentrated hydrochloric acid and obtained the 4-chloro compound. O n diazotization in concentrated sulfuric acid, followed by treatment with water or ethanol, he obtained the corresponding 4-hydroxy or 4ethoxy compounds, respectively (IX-22).
Chemistry of Heterocyclic Compounds: Pyridine and its Derivatives, Part Three, Volume 14