168 Mr Hill, A Series of Substituted Bromanilines. 
with those described in this paper, then the position of the 
bromine atom would be established. This is rather a long process 
and has not yet been completed. 
Methylethylbromaniline. 
This compound has been obtained by Claus and Howitz ( Ber . 
17, p. 1327); but they did not prepare any derivatives. 
It was prepared by the bromination of methylethylaniline in 
acetic acid solution as described above. After liberating with 
potash it was fractionally distilled under reduced pressure. Its 
boiling point is 149° — 152° C. at 13 mms. 
With methyl iodide it readily gave a quaternary iodide; this 
was recrystallised from alcohol, in which it was only slightly 
soluble. Melting point 189° C. 
The picrate first came down as an oil, which afterwards 
crystallised. It was recrystallised several times from alcohol and 
water. Melting point 138° C. 
The base also gave crystalline compounds with ally l and 
iodide. The melting point of the allyl iodide compound 
was 134° C. 
The methyl iodide compound was heated with silver oxide and 
alcohol on the water bath. The solution of hydroxide was filtered 
and evaporated down. It was then distilled, undergoing decom- 
position. The oil which collected in the receiver crystallised on 
standing and, after repeated recrystallisations from alcohol, melted 
at 52° — 53° C. When mixed with dimethyl p-bromaniline its 
melting point was not lowered. 
With methyl iodide it gave a quaternary iodide, melting at 
200° C., identical with the compound which dimethyl p-bromani- 
line forms with methyl iodide. It is thus evident that this de- 
composition product of the hydroxide is dimethyl p-bromaniline. 
Consequently the bromine atom in methylethylbromaniline is in 
the para position. 
Methylisopropylbromaniline. 
This was the first compound of the series to be prepared. 
Methyk'sopropylaniline was first prepared from methylaniline and 
isopropyl bromide. This was then brominated, giving the hydro- 
bromide of methylisopropylbromaniline, which crystallised out on 
evaporating down the acetic acid solution. The hydrobromide was 
more readily obtained by liberating the free base from the acetic 
acid solution, dissolving it in aqueous hydrobromic acid and 
crystallisiug out. 
The hydrobromide could be crystallised from either alcohol or 
water. It melted at 69° C. 
