Page 67 - Org 3 theoritical book 2024-25

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

4) Oxidation:

Oxidation of quinoline with permanganate gives pyridine-2,3-dicarboxylic acid

(quinolinic acid), i.e., the benzene nucleus is easily attacked. Permanganate oxidation

of isoquinoline affords a mixture of phthalic acid and pyridine-3,4-dicarboxylic acid

(cinchomeronic acid).

HOOC
KMnO4
N HOOC N
quinolinic acid

HOOC COOH
KMnO 4 +
N HOOC N COOH

cinchomeronic acid phthalic acid
As previously mentioned, oxidation with peracids gives the corresponding N-oxide.

5) Reduction:

Raney Nickel reduction gives with quinoline 1,2,3.4-tetrahydro and their fully

hydrogenated decahydroquinoline. The same reducing agent gives with isoquinoline

the 1,2,3,4-tetrahydro derivative. All these reduction products are stronger base than

quinoline and isoquinoline.