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Development of a bench-scale pharmaceutical synthesis

Jin, Li (1993) Development of a bench-scale pharmaceutical synthesis. Master of Science thesis, Dublin City University.

Abstract
A straightforward synthesis of 2-methyl-3-trifluoromethyl-aniline has been developed from inexpensive 3-trifluoromethylaniline. Details of the synthetic steps are as follows: (1) conversion of 3-trifluoromethylaniline to pivalylamino-3-trifluoromethylbenzene, (2) conversion of pivalylamino-3-trifluoromethylbenzene to pivalylamino-2-methyl-3-trifluoromethylbenzene, (3) conversion of pivalylamino-2-methyl-3-trifluoromethylbenzene to 2- methyl-3 -trifluoromethylaniline. In attempting a one-step sythesis of 2-(2-methyl-3- trifluoromethylanilino)nicotinic acid from 2-methyl-3-trifluoromethylaniline and 2-chloronicotinic acid, we unexpectedly obtained N-(2- methyl-3-trifluoromethyl)phenyl-2-hydroxynicotinamide. A feasible bench-scale synthetic route to 2-(2-methyl-3- trifluoromethylanilino)nicotinic acid, involving reaction of the methyl ester of 2-chloronicotinic acid with 2-methyl-3-trifluoromethylaniline, has been successfully developed.
Metadata
Item Type:Thesis (Master of Science)
Date of Award:1993
Refereed:No
Supervisor(s):Pratt, Albert
Uncontrolled Keywords:Pharmaceutical chemistry; Drugs Analysis
Subjects:Physical Sciences > Chemistry
DCU Faculties and Centres:DCU Faculties and Schools > Faculty of Science and Health > School of Chemical Sciences
Use License:This item is licensed under a Creative Commons Attribution-NonCommercial-No Derivative Works 3.0 License. View License
ID Code:18961
Deposited On:26 Aug 2013 10:11 by Celine Campbell . Last Modified 25 Apr 2017 14:23
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