An improved and novel synthesis of Olaquindox

ORGN 129

Hari Pati, pati@sask.usask.ca, Umashankar Das, and Jonathan R. Dimmock. College of Pharmacy and Nutrition, University of Saskatchewan, 110 Science Place, Saskatoon, SK S7N 5C9, Canada
Olaquindox has useful antimicrobial , antibacterial properties and in particular it finds use as an animal growth promoter . This compound has been synthesized previously from benzofuroxan which itself is very costly and prepared in several steps. With the goal of devising an efficient and cost effective synthetic pathway to Olaquindox, a completely new route has been devised. In this process, o-phenyldiamine was condensed with 2,3-butanedione and selective oxidation of the resultant quinoxaline led to the corresponding monoaldehyde. Oxidation of the aldehyde group with oxone in methanol led to the corresponding methyl ester which reacted with 2-aminoethanol to produce an amide. Finally oxidation with peracetic acid led to the formation of Olaquindox. Details of the synthetic procedure and the yields obtained will be presented at the conference.
 

Heterocycles, Aromatics, Materials, Devices, Switches, Combinatorial Chemistry, Metal-Mediated Reactions
8:00 PM-10:00 PM, Sunday, 13 March 2005 Convention Center -- Hall D, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, 14 March 2005 Convention Center -- Sails Pavilion, Sci-Mix

Division of Organic Chemistry

The 229th ACS National Meeting, in San Diego, CA, March 13-17, 2005