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Content material:
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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Extra info for Chemistry of Heterocyclic Compounds: Pyridine and its Derivatives, Part Three, Volume 14

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6-Amino-3-nitro-2-picoline yields the 5-chloro derivative (99 Bromo derivatives of 2-aminopyridine were first obtained as byproducts from the Hofmann reaction of 2-picolinamide and potassium hyprobromite ( 5 4 ) . T h e 2-aminopyridine initially formed was probably brominated by excess hypobromite. T h e reported melting points indicate that the 5-bromo and 3,5-dibromo derivatives of 2aminopyridine were present. 69). Extraction of the reaction product with petroleum ether removes the more soluble dibromo compound.

TVitli two moles of nitric acid in sulfuric acid at 85-90’, 4-nitramino-3-nitropyridine is obtained. This compound is also formed by the nitration of 4-nitraminopyridine, but not from 4amino-3-nitropyridine. Sitration a t 170-75” gives 4-amino-5,5-dinitropyridine (388). 3-Aminopyridine forms an N-nitro derivative, but attempted rearrangement in warm sulfuric acid results in decomposition to 3pyridinol (400). Treatment of 3-aminopyridine nitrate with fluorosulfonic acid or liquid hydrogen fluoride gave very low yields of mononitro derivatives of undetermined structure (33).

Warming the nitramino derivative in sulfuric acid failed to effect a rearrangement of the nitro group (398). 2-Methylaminopyridine yields an N-nitro derivative, which rearranges in sulfuric acid to the 3-nitro and 5-nitro derivatives in a ratio of 1: 10. A small amount of N-nitroso-2-methylaminopyridine was also formed (376). 2-Dimethylaminopyridine, which cannot form a nitramino derivative, nevertheless nitrated in high yield to a mixture of the 3- and 5-nitro derivatives in a ratio of 1:9 (317,319).

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