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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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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

Show description

Read or Download Chemistry of Heterocyclic Compounds: Pyridine and its Derivatives, Part Three, Volume 14 PDF

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

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These reactions are more fully discussed on p. 31. I n contrast to alkylation, which requires the sodium salt of the amine, arylations can be performed on the base itself. Thus Chichibabin (304) reported that 2-aminopyridine and bromobenzene J ielded 2-anilinopyridine under the conditions of the Ullman reaction. However, later workers (305) were not able to duplicate his results, but were successful when they substituted iodobenzene for the bromobenzene. 2-Anilinopyridine has also been prepared from 2,2-dichloro-l,2-dihydro-l-phenylpyridine (prepared from 2-pyridone and phosgene) and liquid ammonia (306), and from pyridine and the sodium salt of aniline (7).

12. h'uclear Substitution Reactions (a) Halogenation. In contrast with pyridine itself, aminopyridines halogenate very readil) , and the halogen derivatives thus obtained are useful intermediates for synthesis. Their physical properties are summarized in Tables IX-13 to IX-19 (pp. ). 67). Continued chlorination under these conditions gives 2-amino-3,5-dichloropyridinein 75y0 yield. T h e structure of the monochloro derivative was proved by its preparation from 2,5-diaminopyridine by the Sandmeyer reaction (341).

T h e deamination reaction has been effected with ethanol (352) on diazotized 4-amino-3-pyridinesulfonic acid, and with hypophosphorous acid on diazotized ethyl 5-amino-2-methylnicotinate (6) in 627, yield, Other replacements, generally analogous to procedures in benzene chemistry, have been reported. Potassium ethyl xanthate (357) gives the disulfide (IX-23), mercaptoacetic acid (358) gives pyridylmercaptoacetic acid (IX-24), and copper thiocyanate gives S-thiocyanopyridine (IX-25). 59-362). These reactions fail, however, when the aminopyridine is unsubstituted (276).

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