EHRLICH-SACHS REACTION
1431
spectroscopic data, which are recorded here, 3a, m.p. 90.4ꢀC lit.7 m.p. 91 ꢀC,
1H NMR 2.20 (s, 6H, NMe2), 7.02–7.32 (m, 9H, ArH). IR (KBr); 2130 cm–1.
MS m/e 249 (Mþ) Anal. calc. (found) for C16H15N3 C, 77.11(77.16); H,
6.02(6.12); N, 16.86(16.94). 3b, m.p.127ꢀC, lit.19,20 m.p. 128ꢀC, H NMR
1
2.10 (s, 3H, CH3), 7.6–7.36 (m, 10H, ArH & NH). IR (KBr): 2130 cm–1. MS
m/e 235 (Mþ). Anal. calc. (found) for C15H13N3; C, 76.59(76.64); H,
5.53(5.61); N, 17.87(17.78). 3c, m.p. 170ꢀC, lit.19,20 m.p. 170ꢀC, H NMR
1
7.10–7.42 (m, 10H, ArH). IR (KBr): 2135 cm–1. MS m/e 206 (Mþ), Anal.
calc. (found) for C14H10N2: C, 81.55(81.46); H, 4.85(4.96); N, 13.59(13.64).
3d, m.p. 162ꢀC, lit.23 m.p.. 160ꢀ–167ꢀC, 1H NMR 2.12 (s, 6H, NMe2) 7.04–
7.32 (m, 4H, ArH). IR (KBr): 2125 cm–1. MS m/e 198 (Mþ). Anal. calc.
(found) for C11H10N4; C, 66.66(66.74); H, 5.05(5.13); N, 28.28(28.19). 3e
m.p. 91ꢀC, lit.24 m.p. 91ꢀC, H NMR 2.20 (s, 6H, NMe2), 1.10 (t, 3H,
1
CH2CH3), 4.12 (q, 2H, CH2CH3,) 6.98–7.26 (m, 4H, ArH). IR (KBr):
2130 cm–1 MS m/e 245 (Mþ). Anal. calc. (found) for C13H15N3O2; C,
63.67(63.76); H, 6.12(6.24); N, 17.14(17.22). 3f m.p. 126ꢀC, lit.25 m.p.
126ꢀ–27ꢀC, H NMR 2.12 (s, 6H, NMe2), 7.02–7.36 (m, 9H, ArH). IR
1
(KBr): 2135 cm–1. MS m/e 277 (Mþ). Anal. calc. (found) for C17H15N3O;
C, 76.64(76.55); H, 5.41(5.46); N, 15.16(15.26). 3g, m.p. 223ꢀC, lit.23 m.p.
223ꢀC, H NMR 2.16 (s, 6H, NMe2), 7.10–7.42 (m, 4H, ArH). IR (KBr):
1
2130 cm–1. MS m/e 216 (Mþ). Anal. calc. (found) for C11H12N4O; C,
61.11(61.22); H, 5.55(5.63); N, 25.92(25.99). 3h, m.p. 160ꢀC, lit.23 m.p.
160ꢀC, H NMR 2.12 (s, 6H, NMe2), 7.04–7.42 (m, 10H, ArH & NH), IR
1
(KBr): 2135 cm–1. MS M/e 292 (Mþ). Anal. calc. (found) for C17H16N4O; C,
69.86(69.91); H, 5.48(5.59); N, 19.17(19.19). 3i, m.p. 148ꢀC 1H NMR 1.62 (s,
3H, CH3), 2.16 (s, 6H, NMe2) 7.12–7 45 (m, 8H, ArH). IR (KBr): 2130 cm–1.
MS m/e 263 (Mþ). Anal. calc. (found) for C17H17N3; C, 77.56(77.48); H,
6.46(6.56); N, 15.97(16.05).3j m.p. 77ꢀC, lit.27 m.p. 76ꢀ–79ꢀC. H NMR.
1
2.86 (s, 3H, CH3), 7 12–7.38 (m, 5H, ArH). IR (KBr): 2135 cm–1. MS m/e
299 (Mþ). Anal. calc. (found) for C20H17N3; C, 80.26(80.35); H, 5.68(5.73);
N, 14.04(14.18). 3k, m.p. 159ꢀC, lit.24 m.p. 159ꢀC, H NMR 2.18 (s, 6H,
1
NMe2), 7.02–7.48 (m, 12H, ArH). IR (KBr): 2130 cm–1. MS m/e 188 (Mþ).
Anal. calc. (found) for C10H8N2O2; C, 63.82(63.76); H, 4.25(4.35); N,
14.88(14.94).
REFERENCES
1. Ehrlich, P.; Sachs, F. Ber. 1899, 32, 1179.
2. Krohnke, F.; Krohnke, G. Chem. Ber. 1958, 91, 1474.
3. Colonna, M. Gazz. Chim. Ital. 1960, 90, 117.