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    Pyridine

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    Muhammad AliAli
    Pyridine is a colorless to yellow liquid with the chemical formula C5H5N. It is weakly basic and can be toxic if inhaled or ingested. Pyridine has a structure similar to benzene but with one methine group replaced by a nitrogen atom. It is widely used in pharmaceutical and agrochemical precursors. The Hantzsch synthesis allows the preparation of dihydropyridine derivatives by condensing an aldehyde with two equivalents of a β-ketoester in the presence of ammonia, followed by oxidation to form pyridines. Pyridine undergoes electrophilic substitution at the C-3 position and nucleophilic substitution mainly at C-2.

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    Pyridine

    Uploaded by

    Muhammad AliAli
    77 views16 pages
    Pyridine is a colorless to yellow liquid with the chemical formula C5H5N. It is weakly basic and can be toxic if inhaled or ingested. Pyridine has a structure similar to benzene but with one methine group replaced by a nitrogen atom. It is widely used in pharmaceutical and agrochemical precursors. The Hantzsch synthesis allows the preparation of dihydropyridine derivatives by condensing an aldehyde with two equivalents of a β-ketoester in the presence of ammonia, followed by oxidation to form pyridines. Pyridine undergoes electrophilic substitution at the C-3 position and nucleophilic substitution mainly at C-2.

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    Pyridine is a colorless to yellow liquid with the chemical formula C5H5N. It is weakly basic and can be toxic if inhaled or ingested. Pyridine has a structure similar to benzene but with one methine group replaced by a nitrogen atom. It is widely used in pharmaceutical and agrochemical precursors. The Hantzsch synthesis allows the preparation of dihydropyridine derivatives by condensing an aldehyde with two equivalents of a β-ketoester in the presence of ammonia, followed by oxidation to form pyridines. Pyridine undergoes electrophilic substitution at the C-3 position and nucleophilic substitution mainly at C-2.

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    © All Rights Reserved
    Download as PPTX, PDF, TXT or read online from Scribd
    Download as pptx, pdf, or txt
    77 views16 pages

    Pyridine

    Uploaded by

    Muhammad AliAli
    Pyridine is a colorless to yellow liquid with the chemical formula C5H5N. It is weakly basic and can be toxic if inhaled or ingested. Pyridine has a structure similar to benzene but with one methine group replaced by a nitrogen atom. It is widely used in pharmaceutical and agrochemical precursors. The Hantzsch synthesis allows the preparation of dihydropyridine derivatives by condensing an aldehyde with two equivalents of a β-ketoester in the presence of ammonia, followed by oxidation to form pyridines. Pyridine undergoes electrophilic substitution at the C-3 position and nucleophilic substitution mainly at C-2.

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    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.

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