Pyridine-3-carboxylic acid diethylamide

PYRIDINECARBOXYLIC ACID AMIDE see NCROOO PYRIDINE-3-CARBOXYLIC ACID DIETHYLAMIDE see DJS200... 

Isonicotinic Acid Diethylamide. N.N-Diethytrso-nicotinamide pyridine-4-carboxylic acid diethylamide. C10-H NiO mol wt 178.23, C 67.39%, H 7.92%, N 15,72%, O 8.98%. Prepd by the action of phosphorus oxychloride upon a mixture of isonicotinic acid and diethylamine Carrara,... 

The amides and hydrazides of pyridine-carboxylic acids arc of some importance, though their chemistry is not marked by unusual properties. Nicotinamide is, of course, an important compound, and isonicotinic acid hydrazide (isoniazid) is an antitubercular drug. Substituted derivatives are used as antidepressants. In general, however, these compounds show normal chemical behaviour. The amides undergo hydrolysis, dehydration and Hofmann bromination without difficulty. Their reduction has been much studied as a route to pyridine aldehydes. The Sonn-Muller reduction is not very satisfactory in this series, but the McFadyen-Stevens reaction is useful . Nicotinic acid diethylamide gives only poor yields of the aldehyde upon reduction with lithium aluminium hydride, but yields from the methyl-phenylamide are high. Most satisfactory is the reduction of nicotinic acid dimethylamide with lithium diethoxyaluminium hydride . 

The reagent is prepared by reaction of diethylamine with chlorosulfonic acid methyl ester. In pyridine solution at room temperature it reacts with primary and secondary carboxylic acids after several days to give the carboxylic acid N,N-diethylamide. Tertiary acids and cr-amino acids do not react. ... 

This reagent reacts with primary and secondary carboxylic acids in the presence of pyridine to give A(A-diethylamides (eq 1). The reaction is typically run at rt and requires a long reaction time (several days). In general, tertiary acids and a-amino carboxylic acids do not react. ... 

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