CONTRIBUTION TO CINCHONA ALKALOIDS CHEMISTRY
CONTRIBUTION TO CINCHONA ALKALOIDS CHEMISTRY
CONTRIBUTION TO CINCHONA ALKALOIDS CHEMISTRY
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Ph.D. Thesis Abstract Contribution to cinchona alkaloids chemistry<br />
.<br />
The oxidation reaction occurs in an alkaline medium at a temperature of 90 -<br />
110 o C. After completion of the reaction, the formed cinconidona is extracted in aqueous acid<br />
solution, from which it is released in the alkalinisation of the aqueous solution to pH = 12 and it<br />
is separated by filtration. In table 2.7 there are presented the obtained results.<br />
Nr.<br />
pr<br />
Tabelul 2.7. Optimal conditions of the synthesis process of cinconidinona 41<br />
MATERII PRIME PRODUŞI<br />
Cantitate<br />
CN +<br />
DHCN<br />
(g)<br />
Toluen<br />
NaOH<br />
+<br />
KOH<br />
(g)<br />
H2SO4<br />
(g)<br />
Benzofenonă<br />
(g)<br />
24<br />
CDO<br />
(g)<br />
Umiditate<br />
(%)<br />
CDO<br />
uscat<br />
(g)<br />
1 53,89 415 25+37,1 22 25 81,9 40,1 49,1 91,2<br />
2 55,75 415 25+ 37,1 22 25 86,4 37,2 51,6 92,6<br />
3 55,75 420 25+ 37,1 22 25 86,9 33,3 51,8 91,8<br />
Randament<br />
(%)<br />
The analysis results show that the oxidation reaction of cinchonine to cinchonidinone<br />
using benzophenone as oxidizing agent obtains good yields, from 91.2 to 92.6%. The purity of the<br />
obtained product is over 99%.<br />
2.3.2. Reduction of cinconidinona to cinconidine tartrate<br />
Of the many methods of reducing carbonyl group to hydroxyl functional group described<br />
in the literature we chose borohidrură sodium reduction due to the work conditions and<br />
availability of raw materials. From the reaction mass cinconidine is separated as<br />
tartrate 42. (Scheme 2.17)<br />
Scheme 2.17<br />
N<br />
41<br />
N<br />
O<br />
N<br />
42<br />
NH<br />
OH<br />
2<br />
HC<br />
HC<br />
COO -<br />
COO -<br />
OH<br />
OH
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