[ RO J 
XLUI. 
ON THE PREPARATION OF AMIDOKETONES. 
By PROFESSOR HUGH RYAN, M.A., D.Sc., F.R.U.L., 
Catholic University School of Medicine, Dublin. 
[Read January 16; Received for Publication Marcu 1; 
Published Aucusr 21, 1901.] 
I.—THeoreticat Part. 
By the reduction of isonitrosoketones with tin and hydrochloric 
acid,a series of new and interesting bases were discovered by 
Victor Meyer and his pupils. 
The compounds, then termed ketines, were in all cases liberated 
by the addition of solid caustic potash to a concentrated solution 
of the hydrochloride of the base and distilled over in a current of 
steam. On analysis of the base derived from isonitrosoacetone, it 
appeared to have the formula C;H,,N.0, but after being left some 
time in a vacuum dessicator over sulphuric acid, it gave off one 
molecule of water yielding a base O;H;N., which was afterwards 
identified as dimethylpyrazine. 
The reaction had proceeded in the following manner :— 
(a) 2CH,;:CO-CH:N-OH+4H,+2HO1 
= 2CH; CO CH, NH, HCl+ 2H,0. 
(6) 2CH,;-CO-CH.,°NH,- HCl +2KOH 
= 2CH,: CO: CH,: NH, + 2KCl + 2H.0. 
(c) 2CH;* CO: CH,=NH,0,H.N, : H,0. ; 
Various other methods of preparing amidoketones by the re- 
duction of isonitrosoketones were proposed and unsuccessfully 
attempted. Amongst others it was sought to reduce them by the 
action of 2 and 5 per cent. sodium amalgam on a dilute acid 
solution of the isonitrosoketone. Under these circumstances it was 
found by Gabriel and his pupils that the chief product is the 
corresponding amidoalcohol.' 
1 Ber, 32 (1899), p. 1095. 
SCIENT. PROC. R.D.S., VOL. IX., PART IV. 2Q 
