Mr Hill, A Series of Substituted Bromanilines. 169 
The pure hydrobromide was then decomposed with potash and 
the free base came down as an oil which solidified on cooling. It 
was recrystallised from alcohol several times, giving beautiful 
crystals melting at 34° C. 
Analysis of this base gave the following results: 
0"2075 gram gave 0 4025 gram C0 2 , 0T154 gram ELO. 
C = 52-89, H = 618. 
C :o H 14 BrN requires C = 52 64, H = 614 per cent. 
On mixing with methyl iodide the quaternary iodide slowly 
came down. This was recrystallised from alcohol, in which it was 
fairly soluble. Melting point 167° C. 
The picrate was readily obtained and recrystallised from 
alcohol. Melting point 138° C. 
The base also gave crystalline compounds with allyl and benzyl 
iodide. The allyl iodide melted at 150° C., and on analysis gave 
the following results: 
0-2142 gave 0-3075 C0 2) 0 0978 H„0. C = 39-15, H = 5-07. 
C 13 H ]9 BrNI requires C = 39 39, H = 4‘8. 
The quaternary hydroxide, obtained from the methyl iodide 
compound, on decomposition gave crystals melting at 34° C. 
These were identified as methyh'sopropylbromaniline by means of 
the picrate and methyl iodide compound. 
Methyl-n-propylbromaniline. 
It was prepared in a similar way to the others by the bromina- 
tion of methyl-n-propylaniline. It boiled at 149° — 152° C. at 
5 mms. 
The methyl iodide compound comes down rather slowly and is 
readily soluble in alcohol, from which solution good crystals are 
deposited. It melts at 167° C. 
The picrate is readily formed and, after recrystallising several 
times from alcohol, melted at 126° C. 
The methyl iodide compound gave a quaternary hydroxide, 
which on decomposition gave back the original base. 
Methylisobutylbromaniline. 
Prepared by the bromination of methyh’sobutylaniline. It 
distilled over between 169° and 173° C. at 9 mms. 
The quaternary iodide came down rather slowly on adding 
methyl iodide to the base. After repeated crystallisations from 
alcohol it melted at 167° — 168° C. 
The picrate was formed with the greatest ease and crystallised 
12 
VOL. XIV. PT. II. 
