Page 66 - Org 3 theoritical book 2024-25

Clinical Pharmacy PharmD - 2024/2025 Level 2 Pharmaceutical Organic Chemistry-3 (PC 305)

3- Nucleophilic substitution:

Nucleophiles attack quinoline at the 2- and 4-positions, whereas, in isoquinoline
position 1 is the site of nucleophilic attack.

i. Amination:

Both quinoline and isoquinoline can be aminated via the Chichibabin reaction,

whereby, quinoline gives a mixture of 2- and 4-amino derivatives while the former is

predominant. Isoquinoline gives 1-amino derivative.

ii. Hydroxylation:

The two compounds can be directly hydroxylated by heating with potassium

o
hydroxide at 240 , where carbostyril (2-quinolone) is given with quinoline and
isocarbostyril (1-isoquinolone) with isoquinoline.