340 TRANSACTIONS OF SECTION B. 
SYDNEY. 
FRIDAY, AUGUST 21. 
The following Papers were read :— 
1. Non-Aromatic Diazonium Salts. By Professor GinBert T. Moracan 
and JosePH ReEituy. 
The diazotisability of an organic primary amine is in all probability con- 
nected with the presence in the basic molecule of an unsaturated group, for it 
has not yet been found possible to diazotise the salt of any primary base having 
its amino-group attached directly either to a fully saturated radical or to a com- 
pletely hydrogenised ring. 
It is, however, not essential that the unsaturated radical should be aromatic 
or homocyclic in character, and certain non-aromatic amines are known to 
possess in varying degrees the property of diazotisability. This property has 
been demonstrated in the case of the following heterocyclic bases not merely by 
detecting the presence of diazo-compounds in solution, but also by the isolation of 
the diazonium salts. 
4-Amino-1-phenyl]-2 : 3-dimethylpyrazolone (4-amino-antipyrine) when diazo- 
tised with ethyl nitrite in hydrochloric acid furnishes a well-defined crystallis- 
able diazonium hydrochloride (C,, H,, 0 N, Cl),HCl from which the crystal- 
line dichromate (C,, H,, O N ,),Cr,0,; aurichloride (C,, H,, O N,)AuCl, and 
platinichloride (C,, H,, O N,),PtCl, of normal composition have been prepared. 
4-Amino-3 : 5-dimethylpyrazole, a base containing no aromatic substituent 
whatever, gave rise to a remarkably stable colourless diazonium chloride, crystal- 
lising with great facility, and permanent under ordinary atmospheric conditions. 
Although the parent base forms a dihydrochloride, C, H, N,, 2HCl, one of the 
salt-forming centres disappears in diazotisation, the diazonium chloride 
C, H, N, Cl corresponding in composition with the salt of a monacidic base. 
The replacement of the diazonium group by a triazo-radical restores this 
suppressed salt-forming centre, the product, 4-triazo-3 : 5-dimethyl-pyrazole being 
a basic compound which has the remarkable property of developing character- 
istic colorations with phenols in alkaline solutions, 
Aminomethyltriazole can be diazotised in nitric-acid solution without loss of 
diazo-nitrogen, although in hydrochloric acid effervescence is copious even at 
0° C. 
The diazotisability of wool is usually attributed to the presence in this 
material of aromatic amino- groups; but in view of the foregoing results it 
appears possible that the interaction of wool and nitrous acid may be due in 
part to the presence of heterocyclic rings comparable with those of the pyrazole, 
triazole, or thiazole series. 
2. The Synthesis of Isoquinoline Alkaloids. By Professor R, Ropinson. 
Many pseudo- bases of isoquinoline type—for example, cotarnine, hydra- 
stinine, berberine, isoquinoline methyl hydroxide—readily undergo condensa- 
tions with the most varied classes of organic substances, and the greater 
number of these reactions can be generalised in the scheme :— 
R 
| 
/CHOH -NMe— + HR — —CH—NMe— + H,0 
The interest of these condensations is very much enhanced by the fact that 
they yield substances closely allied in constitution to the naturally occurring 
isoquinoline alkaloids, and for instance cotarnine (I) with meconine (II) gave a 
small yield of a-gnoscopine (III) resolvable by means of d-bromocamphor- 
sulphonic acid into d-narcotine and /-narcotine, the latter proving identical with 
the natural base occurring in opium. Cotarnine and nitromeconine react with 
great facility and give rise to a nitro- base from which by elimination of the 
