Am'Dec.^S7arm'}     Manufacture  of  a-Naplithylamine.  633 
and  the  liberated  alcohol  removed,  a  niethiodide  is  obtained  identical 
with  that  formed  by  the  action  of  methyl  iodide  on  pilocarpidine  at 
60°.  The  hydroxy methylpilocarpidine  obtained  by  the  action  of  sil- 
ver oxide  on  the  corresponding  methiodide,  yields  pilocarpidine  when 
boiled  with  water.  These  results  show  that  it  is  difficult  if  not  im- 
possible to  remove  the  methyl  hydroxide  from  position  (1),  and  re- 
place it  by  methyl  hydroxide  in  position  (2). 
When,  however,  pilocarpidiue  methiodide  is  oxidized  by  means  of 
silver  permanganate,  an  unstable  group,  MeN(1)  Mn04,  is  formed,  and 
decomposes  without  affecting  the  remainder  of  the  molecule.  An 
aqueous  solution  of  pilocarpidine  methiodide  is  mixed  with  silver  per- 
manganate until  the  greater  part  of  the  silver  iodide  is  precipitated. 
Oxidation  takes  place  immediately,  and  the  liquid  contains  pilocarpine 
and  formic  acid.  The  alkaloid  is  liberated  by  addition  of  potassium 
carbonate,  and  yields  the  aurochloride  AuCl3,C11H16X02,  melting  at 
88°.  Synthetical  pilocarpidine  and  pilocarpine  yield  gummy  deriva- 
tives similar  to  those  obtained  by  Harnack  and  Meyer  from  the  na- 
tural products.  This  phenomenon  is  confined  to  the  gold  compounds, 
and  is  purely  physical. 
The  physiological  action  of  synthetical  pilocarpine  is  identical  with 
that  of  the  natural  alkaloid. 
MANUFACTURE  OF  a-NAPHTHYL AMINE.1 
By  0.  N.  Witt. 
An  important  feature  in  the  success  attending  the  manufacture  of 
naphthylamine  is  the  purity  of  the  naphthalene  employed.  The  ni- 
tration is  effected  in  cast-iron  cylinders  fitted  with  stirrers  and  cooling 
jacket.  The  charge  consists  of  250  kilos,  of  naphthalene,  200  kilos,  of 
nitric  acid  of  40°  Baume,  200  kilos,  of  sulphuric  acid  of  66°  Baume, 
and  600  kilos,  of  the  waste  acid  from  a  previous  nitration,  the  latter 
being  used  as  diluent.  The  nitration  is  performed  at  45-50°,  the 
temperature  being  regulated  by  the  rate  at  which  the  naphthalene  is 
added  and  the  flow  of  cold  water  through  the  cooling  jacket.  The  re- 
action is  completed  in  about  12  hours.  The  contents  of  the  apparatus 
are  then  transferred  to  wooden  vats  lined  with  lead  and  allowed  to 
^Ding.  polyt.  Jour.,  vol.  265,  pp.  225-230;  reprinted  from  Jour.  Chem.  Soc. 
November. 
