Doebner-Miller reaction and applications

Seemanta Nayan Das

1. Doebner -Miller Reaction : Me chanism and its Applications Subject:- Advanced Organic Chemistry - 1 Subject Code:- MPC 102T Presented by- Seemanta Nayan Das M.Pharm 1 st semester Presented to - Dr. Smriti Rekha Chanda Das Associate Professor Department of Pharmaceutical Chemistry 1

2. Contents Introduction to Doebner -Miller Reaction. Mechanistic pathway. Application of Doebner -Miller Reaction. Bibliography 2

3. Introduction to Doebner -Miller Reaction This reaction was initiated by Doebner and von Miller in 1881 as a modification of original Skarup reaction and later modified by Beyer in 1886. Doebner -Miller reaction is an organic reaction which is an acidic condensation between primary amines (e.g. aniline) and α , β – unsaturated carbonyl compounds to obtain quinolines . This reaction can also be named as Skarup-Doebner von Miller quinoline synthesis. 3

4. Mechanistic pathway 4

5. Mechanistic pathway 5

6. 6 Application of Doebner -Miller Reaction This reaction is generally used for the synthesis of quinolines with substituents on the pyridinoid ring . The synthesis of quinoline from this reaction is used as a precursor to 8-hydroxyquinoline which is a chelating agent and precursor to pesticides.

7. Bibliography Wang, Zerong . (2010). Comprehensive Organic Name Reactions and Reagents || Doebner -Miller Reaction. , 10.1002/9780470638859(), –. doi:10.1002/9780470638859.conrr198 D oebner -miller- quinoline -synthesis https://images.app.goo.gl/zcwcGUjfJExdCTZS6 Date- 24/08/2024. Time: 08:15 pm 7

8. Thank you 8