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Quinine

The famous Rabe-Kindler quinine synthesis was repeated in 2008. The experimental details given were gathered from the 2008 article.

Chemical structure of Quinine
C20H24N2O2
Author Paul Rabe
Publication year 1918
Synthesis type Partial synthesis
Number of steps 3 (linear)
References

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Part 1 of 1
Chemical structure
NaOBr, HCl
Et2O, H2O
RT, 24 h, 55%

The starting material (quinotoxine) was obtained from the degradation of natural quinine.
Chemical structure
NaOEt
EtOH
Reflux, 10 min, 88%

Selectivity : 50:50
See the Hofmann-Löffler-Freytag Reaction
Chemical structure
Al, NaOEt
EtOH
Reflux, 2 h, 5%

See the Meerwein-Ponndorf-Verley Reduction
(-)-Quinine was selectively cristallized (as a tartrate salt) from the resulting four diastereoisomers.
Chemical structure

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