EUDESMIN AND ITS DERIVATIVES. 459 
acid (D = 1°42, 10 ccm.) and acetic acid (15 ccm.) gradually 
added. When all the nitric acid had been added, the nitro 
derivative crystallised from the solution, and, after five 
minutes, the mixture was diluted with water, the pre- 
cipitate collected, washed with water, dried and crystallised 
first from acetic acid and then from ethyl acetate. The 
substance is, when freshly prepared, almost colourless and 
crystallises from all solvents in the form of extremely 
slender needles, which fill the whole solution. It melts 
without decomposition at 214°. 
9°1275 gave 0°2608 CO2 and 0°0582 H2O. C =55°8sy H=5'1. 
0°1242 gave 5°9 ccm. Ne reduced to N.T.P. N = 6°0. 
C22H210¢6(NO2)2 requires C = 55°5, H=5'0, N=5'9 per cent. 
Dinitroeudesmin turns yellow on exposure to light, and 
dissolves in sulphuric acid to a bright red solution. It is 
unchanged by treatment with nitric acid in the cold, and 
is perfectly stable to bromine in carbon disulphide solution. 
It is readily soluble in chloroform but sparingly so in other 
solvents, and remarkably sparingly soluble in alcohol. It 
may be easily reduced by means of tin and hydrochloric 
acid, but the corresponding amine is unstable and undergoes 
some decomposition in acid solution, which will be further 
investigated. The solution of the aminoeudesmin obtained 
by elimination of the tin with hydrogen sulphide gives a 
bright blue colour with ferric chloride, and exhibits the 
diazo reaction. The constitution of dinitroeudesmin as 
regards the position of the groups directly attached to the 
benzene nuclei is clearly proved by the experiment 
described in the next section. 
SIMULTANEOUS OXIDATION AND NITRATION OF EUDESMIN ; 
FORMATION OF 4: 5—DINITROVERATROL. 
Eudesmin (1 gr.) was boiled for ten minutes with ordinary 
concentrated nitric acid (10 ccm.) when the substance was 
oxidised and a large amount of nitrous fumes evolved. The 
