DawooD University Of Engineering And Technology

Topic:- Chemstry Of pyridine

Name: Muhammad Ali

Roll No: 22F-BSCHY-13
Subject: Organic Chemistry
Submitted To: Sir Pervaiz
 Pyridine
Introduction:-
What is Pyridine?
Pyridine is a heterocyclic compound which is a colourless to yellow liquid with a
chemical formula C5H5N.
It is a basic heterocyclic organic compound. It is also known as Azine or
Pyridine. The structure is like benzene, with one methine group replaced
It is weakly basic and is miscible with water.
It is highly flammable and when inhaled or ingested it becomes toxic. Some
symptoms, when exposed to pyridine, are nausea, asthmatic breathing, vomiting,
headache, laryngitis, and coughing.
It is widely used in the precursor to agrochemicals and pharmaceuticals. Also, it is
used as an important reagent and organic solvent. by a nitrogen atom.
Pyridine Structure
 Properties of Pyridine – C5H5N
Pyridine and its simple derivatives are stable and relatively unreactive liquids,
with strong penetrating odours that are unpleasant. Pyridine is the hydrogen
derivative of this ring, it is benzene in which one CH- or methine group is
replaced by a nitrogen atom. The structure of pyridine is completely analogous
to that of benzene, being related by the replacement of CH with N.
C5H5N Pyridine

Molecular Weight/ Molar Mass 79.1 g/mol

Density 982 kg/m³

Boiling Point 115 °C

Melting Point −41.6 °C

 Hantzsch Dihydropyridine (Pyridine) Synthesis

This reaction allows the preparation of dihydropyridine derivatives by condensation of an aldehyde

with two equivalents of a β-ketoester in the presence of ammonia. Subsequent oxidation (or
dehydrogenation) gives pyridine-3,5-dicarboxylates, which may also be decarboxylated to yield the
corresponding pyridines.
Mechanism of the Hantzsch Dihydropyridine Synthesis:-

The reaction can be visualized as proceeding through a Knoevenagel Condensation

 product as a key intermediate:

A second key intermediate is an ester enamine, which is produced by condensation of

the second equivalent of the β-ketoester with ammonia.

Further condensation between these two fragments gives the dihydropyridine

derivative:
 Preparation Methods:-
1. By passing a mixture of acetylene and hydrogen cyanide through a red- hot tube.
2. By dehydrogenation of piperidine with concentrated sulphuric acid at
300°C or with nitrobenzene at 260°C.
3. By heating tetrahydrofurfuryl alcohol with ammonia in the presence of aluminium oxide at
500°C. (Commercial Method of Preparation).
 Chemical properties of Pyridine

1. Basic Character: Pyridine behaves as a base. It reacts with acids to form fairly stable salts..
2. Electrophilic Substitution: Pyridine, however, does undergo electrophilic Substitution reactions
when extremely vigorous reaction conditions are used. Substitution occurs almost exclusively at C-3
(β-Position).
3. Nucleophilic Substitution:
Pyridine undergoes nucleophilic substitution reactions mainly at C-2 (or at
C-4 if C-2 is blocked)
Oxidation: Like benzene, pyridine is quite stable towards mild oxidizing
agents. It does not react with chromic acid or nitric acid. However, it may be
oxidized by peracetic acid to give pyridine-N-oxide.