Am.  Jour.  Pharm. ) 
Mar.,  1881.  J 
jReseai'ches  on  the  Cinchona  Alkaloids. 
105 
RESEARCHES  ON  THE  CONSTITUTION  OF  THE  CIN- 
CHONA ALKALOIDS. 
By  O.  Hesse. 
Ueprint  from  Liehig's  "Annalen  der  Cliemie,"  Baud  205, pp.  314  to  357,  1880.  Communicated  by  the  authof. 
Translated  and  condensed  for  the  "  Journal "  ))y  Frederick  B.  Power. 
As  is  well-known,  a  great  deal  of  uncertainty  still  prevails  in  regard 
to  the  condition  in  which  theoxvffen  is  contained  in  the  more  common 
"Cinchona  alkaloids. 
Zorn  (^^  Journ.  fiir  prakt.  Chemie"  [2],  8,  279)  believes  to  have 
proved  the  presence  of  hydroxyl  in  these  alkaloids,  in  that  he  has  sup- 
posed to  have  found  that  by  the  action  of  highly  concentrated  hydro- 
ohloric  acid  upon  these  bases,  tlie  hydroxyl  may  be  exchanged  for 
•chlorine;  the  further  statements  of  Zorn,  however,  in  regard  to  the 
supposed  chlorides,  influenced  the  author  to  regard  these  bodies  as 
addition  products  (Liebig's  ^'Annalen,"  Bd.  174,  p.  340).  This  view, 
indeed,  did  not  meet  with  the  acceptance  of  Zorn  (^Mourn.  fiir  prakt. 
Chem."  [2],  14,  281).  According  to  the  author's  supposition,  the 
hydroxyl  groups,  if  such  were  really  present,  should  have  become 
transferred  to  the  new  bodies,  and  there  remained,  therefore,  after  the 
opposition  of  Zorn,  nothing  further  than  to  examine  whether,  in  the 
first  place,  with  the  original  alkaloids,  and  then  with  their  respective 
derivatives,  evidences  were  at  hand  which  would  speak  indubitably 
for  the  presence  or  absence  of  hydroxyl  groups  therein. 
For  the  solution  of  the  problem  the 'study  of  the  behavior  of  these 
bodies  bodies  towards  acetic  anhydride  appeared  to  be  the  most  suit- 
able, with  the  view  that  if  hydroxyl  were  really  present  it  would,  by 
proper  treatment,  be  converted  into  acetoxyl. 
1.  Action  of  Acetic  Anhydride  on  the  directly  obtainable  Cinchona 
alkaloids} — It  is  stated  by  Wright  and  Beckett  ('^  Jahresber.  fiir 
Chem.,''  etc.,  1876,  p.  813)  that  by  the  action  of  acetic  anhydride  upon 
quinia  and  quinidia  (conquinia),  acetylquinicia,  and  by  the  action  .of 
the  same  upon  cinchonidia  and  cinchonia,  acetyl-cinchonicia  is  formed. 
The  author  has  found  that  when  the  before-mentioned  alkaloids, 
homocinchonidia  included,  are  treated  with  acetic  anhydride  at  60° 
to  8()°C.,  the  acetic  ethers  of  the  same  are  formed;  instead  of  the  free 
^  Homo-cinclionidia  has  been  included  in  tliis  investigation,  as  from  the 
statements  of  Zorn  it  is  undecided  whether  lie  worked  with  cinchonidia, 
homocinchonidia  or  a  mixture  of  the  two. 
