VOL.
XXIV.
No. 1 1 .
[NOVEMBER, 1902. ]
THE JOURNAL OF THE
AMERICAN CHEMICAL SOCIETY. [CONTRIBUTION FROM T H E HAVEMEYER LABORATORIES, COLUMBIA U N I VERSITY, NO. 70.1
THE SYNTHESIS OF ALKYLKETODIHYDROQUINAZOLINES FROM ANTHRANILIC NITRILE.' BY
.MARSTON TAYLOR BOGEBTAND WILLIAM FLOWERSHAND. Received July 31,
xpol.
THEORETICAL PART.
BOCERTAND GOTTHELFhave already shownZ that ketodihydroquinazolines may be prepared by heating together in sealed tubes anthranilic acid, or its acyl derivatives, with a nitrile, and the reactions there suggested in explanation of this synthesis, taking the case where an acylanthranilic acid was the starting-point, were as follows: / N H . CO. CH, / N H . CO. CH, CH,CN = C,H, C,H, \COOH \CO.NH. CO.CH, ,N-C-CH, / , ............................ ? .......................... /N=C-CH, / / I II :. -I j.H ................................ O C"~\co-NH \CO-NH--~CO-CH,/ ............................ CH,.COOH.
+
j
+
I t will be seen upon examining the structure of the hypo1 Read before the New,York Section of the American Chemical Society, at its meeting January 24, 1 9 2 . 1 This Journal, aa, 13 and 512 : 23, 611.
1032
MARSTON TAYLOR BOGEKT A N D WILLIAX F . H A N D .
thetical intermediate product, the secondary amide, that the -CO-NH-CO-group being symmetrical should be formed equally well from R C N R . C O O H as from R C N R.COOH ; in other words, as the condensation takes place solely between the CK and C O O H it is immaterial which radical carries the CN and which the COOH. This same secondary amide should therefore result when acetylanthranilic nitrile is heated with acetic acid, as follows:
+
NH.CO.CH, ““4
