Page 67 - Pharmaceutical Organic Chemmistry-3 (Theoritical book) 24-25

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

Sulphonation of quinoline gives the 8-derivative which is converted to the 6- isomer at
high temperature, however, both 5- and 8-sulphonic acids are isomerized to the 6-

isomer. On the other hand, isoquinoline affords the 5-sulphonic acid.

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.