This document discusses the properties, synthesis, and reactions of quinoline and isoquinoline. Quinoline and isoquinoline are aromatic and undergo nucleophilic substitution reactions readily. Key synthesis methods discussed include the Skraup, Doebner-Miller, Friedlander, Bischler-Napieralski, Pictet-Gams, and Pomeranz-Fritsch reactions. The document also outlines various electrophilic addition, substitution, reduction, oxidation, and nucleophilic substitution reactions that quinoline and isoquinoline undergo. Finally, some medicinal uses of quinoline and isoquinoline are mentioned.

1. Q U I N O L I N E and ISO-Q U I N O L I N E
Dr Akhil Nagar
RCP-IPER

2. Q U I N O L I N E and ISO-Q U I N O L I N E

3. Properties
1. Aromatic
Q U I N O L I N E
• Weak Base: As both quinoline and isoquinoline are similar like pyridine,
where nitrogen electron pair are not involved in the conjugation with ring.
Both undergoes nucleophilic substitution reaction readily on heterocyclic
ring and electrophilic substitution more readily than pyridine.

4. Synthesis
1. Skraup Quinoline synthesis

5. Synthesis
1. Skraup Quinoline synthesis
Mechanism

8. Synthesis
2. Doebner-Miller Synthesis
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9. The Reaction is possible in the presence of
Aniline + Aromatic amine + 2 mole of Acetaldehyde
in presence of HCl.

10. Synthesis
3. Friedlander Synthesis
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11. Synthesis
3. Friedlander Synthesis

12. • Pfitzinger Reaction: Modified Friedlander synthesis.
• The O- aminobenzaldehyde is unstable and can be replaced
with Isatin to give Isotoic acid, which forms shiff base and in
presence of base it gives quinoline.

13. Reactions
1. Electrophilic addition to N

14. Reactions
2. Electrophilic aromatic substitution

15. Reactions
3. Reduction reactions
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16. Reactions
4. Oxidation
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17. 153
Reactions
5. Nucleophilic substitution
If the C-2 position is occupied then the nucleophilic attack will be
preferred at C-4 position.

18. Medicinal uses
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19. Medicinal uses
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20. Properties
1. Aromatic
I S O Q U I N O L I N E
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21. Synthesis
1. Bischler-Napieralski Isoquinoline synthesis
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23. Synthesis
2. The Pictet – Gams synthesis
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25. Synthesis
3. Pomeranz–Fritsch synthesis
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Reactions
1. Electrophilic addition to N

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Reactions
2. Electrophilic aromatic substitution

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Reactions
3. Reduction reactions

30. I S O Q U I N O L I N E
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Reactions
4. Oxidation

31. I S O Q U I N O L I N E
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Reactions
5. Nucleophilic substitution

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Medicinal uses

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Medicinal uses