indole

2. Dr. Sajid Hussain
(Faculty of Pharmacy)
The University of Lahore
Group#9
Presented by:
Mubashar Ali 151
Bilawal Mughal 144
Summer Nisar 251
Rana Muhammad Yasir 244
Shehzad Anwar 247
Umar Hayat 035
M.Asad Iqbal 063
Junaid Ghaffar 134
ORGANIC PRESENTATION
Presented To:

3. INDOLE
Definition:
Indole contains a benzene ring fused with a pyrrole ring at C-2/C-3, and can be described
as benzopyrrole. Indole is a ten p electron aromatic system achieved from the delocalization of the
lone pair of electrons on the nitrogen atom. Benzofuran and benzothiaphene are very similar to
benzopyrrole (indole), with different hetero-atoms, oxygen and sulphur respectively.

4. STRUCTURE:

5. GENERAL FORMULA:
Its chemical formula is C8H7N.
Discovery:
Indole as first prepared in 1866 by zinc dust distillation of oxindole.

6. OCCURANCE:
 indole is a solid at room temperature.
 It occurs naturally in human feces and has an intense fecal odor.
 It also occur in coal tar.
 it is constituent of many flower scents and perfumes.

7. PHYSICAL PROPERTIES:
 Weak basic compound
 Conjugate acid of indole is strong acid (pKa = –2.4).
 White solid at room temperature.
 Boiling point (253-254 *C)
 Melting point (52-54 *C)
 Slightly soluble in water, readily soluble in organic solvents, e.g. Ethanol,ether and benzene

8. CHEMICAL PROPERTIES:
 Solid at room temperature
 Corresponding substituent is called indolyl.
 Chemical formula is C8H7N.

9. REACTIONS:
Electrophilic aromatic substitution Electrophilic aromatic substitution of indole
occurs on the five-membered pyrrole ring, because it is more reactive towards
such reaction than a benzene ring. As an electron-rich heterocycle, indole
undergoes electrophilic aromatic substitution primarily at C-3, for example
bromination of indole.

11. SYNTHESIS:
Indole is synthesised by these steps:
 Fischer Indole Synthesis
 Leimgruber Synthesis

12. FISCHER INDOLE SYNTHESIS
Cyclization of arylhydrazones by heating with an acid or Lewis acid catalyst yields an indole
system. The most commonly used catalyst is ZnCl2. The disadvantage of this reaction is that
unsymmetrical ketones give mixtures of indoles if R’ also has an ᾱ-methylene group.

13. LEIMBRUBER SYNTHESIS:
Aminomethylenation of nitrotoluene followed by hydrogenation yield indole.

14. USES:
 Preventing breast cancer, colon cancer, and other types of cancer
 Early research shows that taking indole-3-carbinol by mouth helps treat cervical dysplasia
 Fibromyalgia.

15. PHARMACEUTICAL PRODUCTS:
Drug
Name
Medication
Ziprasidone For the treatment of schizophrenia and related
psychotic disorders.
Molindone Molindone is used for the management of the
manifestations of psychotic disorders.
Sertindole Used in the treatment of schizophrenia.
Lurasidone Treatment of schizophrenia.