Quinoline is a heterocyclic organic compound. The chemical name of quinoline is alpha, beta benzopyridine. The molecular formula for quinoline is C9H7N. In the quinoline molecular formula, then C represents the carbon, H represents the hydrogen and the numbers written in subscript represent the number of respective elements. Quinoline is found in coal tar and bore oil.
Structure of Quinoline
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Quinoline consists of a benzene ring fused to the alpha-beta-position of the pyridine ring. In the quinoline structure, there are five double bonds present and eleven single bonds are present. The single bonds are sigma bonds formed by the head-on overlapping. The double bond consists of one sigma bond and one pi bond. The pi bonds are formed by the lateral overlapping of the p orbitals.
Preparation Methods of Quinoline
1. Skraup Synthesis Method-
This method is the most widely used method for the preparation of quinoline. In this method, aniline and glycerol are heated at a high temperature in the presence of sulphuric acid and mild oxidizing agents like nitrobenzene or the presence of peroxides like arsenic peroxide. Ferrous sulphate (FeSO4) or boric acid (H3BO3) is generally added to make the reaction less violent because skraup synthesis is a highly exothermic reaction.
Mechanism of Skraup Synthesis Method:
Step 1: In this step, glycerol undergoes a dehydration reaction in the presence of sulphuric acid to give acrolein.
Step 2: In this step, the above-formed acrolein reacts with the aniline and forms an intermediate as a product of this reaction.
Step 3: In this method the cyclization of the intermediate takes place. This cyclization process occurs in the presence of concentrated sulphuric acid to form 1, 2-dihydro quinoline.
Step 4: In this step, the oxidation of 1,2-dihydroquinoline takes place on the reaction with nitrobenzene. On reacting with nitrobenzene, 1,2-dihydroquinoline forms the quinoline as a product.
2. Friedlander Synthesis-
In this method, ortho- amino benzaldehyde is condensed with acetaldehyde in the presence of sodium hydroxide (NaOH) solution by the cyclisation process.
Miller Synthesis- Primary aryl amines with free ortho positions can react with the alpha, beta-unsaturated carbonyl compound in the presence of acid to yield quinolines.
4. Knorr Quinoline Synthesis-
In this reaction, the condensation of aniline takes place with the beta- ketoester at a high temperature to give an anilide intermediate. This formed anilide intermediate undergoes the cyclisation process. The concentrated sulphuric acid is added to the reaction for the dehydration process. The dehydration phenomena lead to the production of 2-hydroxyquinolines.
Properties of Quinoline
Physical Properties of Quinoline
Quinoline is a colourless liquid chemical.
The boiling point of the quinoline is 237 degrees celsius.
Quinoline is composed of a large number of hydrophobic carbon chains that makes it sparingly soluble in water.
Quinoline is soluble in organic solvents.
The nature of quinoline is basic due to the presence of the pyridine ring. In the pyridine ring, the lone pair is present on the nitrogen atom. Therefore, it can donate a lone pair of electrons, hence, basic.
Chemical Properties of Quinoline
Quinoline gives an electrophilic substitution reaction due to the presence of resonance phenomena in the molecule.
Quinoline gives a nitration reaction in the presence of concentrated nitric acid and concentrated sulphuric acid.
Quinoline gives a bromination reaction in the presence of bromine and silver sulphate.
Quinoline compound reacts with the potassium permanganate and undergoes the oxidation reaction. In the oxidation process quinoline gets converted into nicotinic acid.
Quinoline undergoes a reduction reaction in the presence of tin and hydrochloric acid and gets converted into decahydroquinoline.
Some Important Compounds of Quinoline
1. Quinoline Yellow-
Quinoline yellow is a derivative of quinoline. It is used as a colouring agent. Quinoline yellow is a member of quinolines, a beta-diketone and an aromatic ketone. The molecular formula of quinoline is C18H11NO2. The chemical name of quinoline is quinophthalone. The molecular weight of quinoline is 273.3 g/mol. The structure of quinoline yellow is given below:
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2. Chloro Hydroxy Quinoline-
Quinoline Yellow dye can be prepared by sulfonating the compound 2-(2-quinolyl) indan-1,3-dione or by a mixture that contains about two-thirds of 2-(2-quinolyl)indane-1,3-dione and one-third of 2-(2-(6-methylquinolyl)) indane-1,3-dione. Quinoline yellow dye compound consists of essentially sodium salts of a mixture of di sulfonates, mono sulfonates and tri sulfonates of the above-mentioned compound.
3. Amino Quinoline-
Amino quinoline is a derivative of quinoline. The hydrogen at the eighth position is replaced by the amino group. Therefore, also known as the eight amino derivatives of quinoline. The structure of amino quinoline is analogous to that of 8-hydroxyquinoline. The structure of amino quinoline is shown below:
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4. Chloro Quinoline-
Chloro quinoline is a derivative of quinoline. The molecular formula of chloro quinoline is C9H6CIN. The molecular weight of chloro quinoline is 163.6 g/mol.
5. Hydroxy Chloro Quinoline-
Hydroxy chloro quinoline is a chemical compound that is a derivative of quinoline. It possesses antimalarial and anti-inflammatory properties. Hydroxyquinoline is a chemical that contains amino groups. The function of hydroxy chloro quinoline is similar to that of chloroquine.
Chloro Hydroxy Quinoline Uses:
Chloro hydroxy quinone is used as an immunosuppressive drug.
chloro hydroxyquinoline is used as a substitute for antimalarial drug.
It is used for the treatment of dreadful diseases like cancer, for killing tumour cells.
Sar of Quinolines
SAR of quinolines stands for the similar structure-activity relationship of quinolines. The study of quinolines is necessary for the comparison of the antimalarial activity. The asymmetry at the third carbon and fourth carbon is not necessary for the antimalarial activity. The substitution of the halogen group at eight carbon positions will increase the antimalarial activity of the drug. The presence of a methoxy group is not necessary for the antimalarial activity.
Quinoline is an aromatic compound, used mainly for the production of intermediate compounds in the manufacture of other products.
It is used in agriculture for the raising and farming of animals and growing of crops.
It is used as an agrochemical.
Its materials are used in the building process, such as flooring, insulation, caulk, tile, wood, glass, etc.
It is used as chemicals in cigarettes, or tobacco-related products, or related to the manufacturing of tobacco products.
Did You Know?
Quinoline is also known as quinoline yellow lake, due to its yellow colour. It is an aluminium salt of quinoline.
The alkaloids of quinoline can be derived from rutaceous plants.
Quinoline is slightly basic.