Tahere RAHI et al. / Chinese Journal of Catalysis, 2012, 33: 1095–1100
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(s), 1550 (vs), 1380 (s), 1090 (s), 870 (s), 730 (s), 690 (s). H
16.59; Found: C, 66.22; H, 4.22; N, 16.38.
NMR (300 MHz, CDCl3): į 4.05 (brs, 1H), 5.70 (s, 1H), 6.79
(dd, 2H, J1 = 8.57 Hz, J2 = 0.75 Hz), 6.94 (t, 1H, J = 7.35 Hz),
7.27–7.32 (m, 2H), 7.39 (dd, 1H, J1 = 8.28 Hz, J2 = 2.07 Hz),
7.53 (d, 1H, J = 2.07 Hz), 7.70 (d, 1H, J = 8.48 Hz). 13C NMR
(75 MHz, CDCl3): į 47.69, 114.41, 117.39, 120.76, 128.14,
129.66, 129.89, 130.42, 134.35, 136.54, 144.32. Anal. Calcd
for C14H10Cl2N2: C, 60.67; H, 3.64; N, 10.11; Found: C, 60.47;
H, 3.37; N, 9.93.
Phenylamino-thiophen-2-yl)-acetonitrile (1i): white cream
o
o
solid; recrystallized from ethanol; m.p. 97–99 C (98–100 C
[11]). IR (KBr, cm–1): Ȟ 3357 (s), 3100 (m), 2237 (m), 1599 (s),
1500 (vs), 1436 (s), 1348 (s), 1252 (s), 1149 (s), 1063 (s), 884
(s), 833 (s), 751 (s). 1H NMR (300 MHz, CDCl3): į 4.20 (d, 1H,
J = 8.9 Hz), 5.58 (d, 1H, J = 9.2 Hz), 6.74 (d, 2H, J = 7.6 Hz),
6.89 (t, 1H, J = 7.4 Hz), 7.00 (q, 1H, J = 2.8 Hz), 7.21–7.33 (m,
4H). 13C NMR (75 MHz, CDCl3): į 46.1, 114.5, 117.5, 120.6,
127.01, 127.07, 127.13, 129.5, 136.8, 144.1. Anal calcd for
C12H10N2S: C, 67.26; H, 4.70; N, 13.07; Found: C, 67.30; H,
4.75; N, 12.98.
(4-Methoxy-phenyl)-phenylamino-acetonitrile (1e): white
o
o
solid; recrystallized from ethanol; m.p. 95–97 C (94–95 C
[8]). IR (KBr, cm–1): Ȟ 3340 (s), 2920 (s), 2235 (m), 1590 (s),
1500 (vs), 1300 (s), 1240 (s), 1180 (s), 1020 (s), 822 (s), 745
(s), 690 (s). 1H NMR (300 MHz, CDCl3): į 3.86 (s, 3H), 4.01
(brs, 1H), 5.38 (s, 1H), 6.80 (d, 2H, J = 7.5 Hz), 6.92 (t, 1H, J =
7.4 Hz), 6.99 (d, 2H, J = 8.7 Hz), 7.29 (dd, 2H, J1 = 7.2 Hz, J2 =
1.2 Hz), 7.53 (d, 2H, J = 8.5 Hz). 13C NMR (75 MHz, CDCl3): į
49.71, 55.46, 114.15, 114.68, 118.45, 120.22, 126, 128.65,
129.58, 144.77, 160.48. Anal. Calcd for C15H14N2O: C, 75.61;
H, 5.92; N, 11.76; Found: C, 75.41; H, 5.84; N, 11.60.
2-Phenylamino-hexanenitrile
(1j):
white
solid;
recrystallized from ethanol; m.p. 55–57 oC (56–58 oC [10]). IR
(KBr, cm–1): Ȟ 3351 (s), 2233 (m). 1H NMR (300 MHz,
CDCl3): į 0.85 (t, 3H, J = 6.7 Hz), 1.20–1.40 (m, 2H),
1.53–1.60 (m, 2H), 3.15 (q, 2H, J = 6.7 Hz), 3.97–4.16 (m, 2H),
6.98–7.31 (m, 5H). Anal. Calcd for C12H16N2: C, 76.55; H,
8.57; N, 14.88; Found: C, 76.51; H, 8.66; N, 14.83.
2-Benzylamino-3-methyl-butyronitrile (1k): colorless oil
[6]. IR (KBr, cm–1): Ȟ 3347 (s), 2223 (m). 1H NMR (300 MHz,
CDCl3): į 1.07 (d, 3H, J = 6.7 Hz), 1.08 (d, 3H, J = 6.8 HZ),
1.55 (brs, 1H), 1.96–1.99 (m, 1H), 3.25 (d, 1H, J = 6.0 Hz),
3.79 (d, 1H, J = 13.0 Hz), 4.06 (d, 1H, J = 13.0 Hz), 7.23–7.36
(m, 5H). 13C NMR (75 MHz, CDCl3): į 18.2, 19.2, 31.5, 51.7,
56.2, 119.2, 127.4, 128.4, 128.5, 138.3. Anal. Calcd for
C12H16N2: C, 76.55; H, 8.57; N, 14.88; Found: C, 76.41; H,
8.48; N, 14.65.
(3,4,5-Trimethoxy-phenyl)-phenylamino-acetonitrile (1f):
white solid; recrystallized from ethanol; m.p. 147–149 oC
(147–149 oC [14]). IR (KBr, cm–1): Ȟ 3340 (s), 2950 (s), 2228
(s), 1595 (s), 1498 (vs), 1460 (s), 1422 (s), 1230 (s), 1125 (s),
1100 (s), 820 (s), 760 (s), 690 (s). 1H NMR (300 MHz, CDCl3):
į 3.89 (s, 3H), 3.91 (s, 6H), 4.1 (brs, 1H), 5.39 (s, 1H),
6.80–6.83 (m, 4H), 6.94 (t, 1H, J = 7.4 Hz), 7.28–7.34 (m, 2H).
13C NMR (75 MHz, CDCl3): į 50.51, 56.35, 60.93, 104.36,
114.20, 118.20, 120.43, 129.34, 129.63, 144.67, 153.87. Anal.
Calcd for C17H18N2O3: C, 68.44; H, 6.08; N, 9.09; Found: C,
68.35; H, 5.98; N, 9.0.
Morpholine-4-yl-phenyl-acetonitrile (1l): white solid; re-
o
o
crystallized from ethanol; m.p. 69–71 C (68–69 C [6]). IR
(KBr, cm–1): Ȟ 2820 (s), 2230 (m), 1450 (vs), 1284 (s), 1110 (s),
1002 (s), 915 (s), 862 (s), 738 (s), 684 (s). 1H NMR (300 MHz,
CDCl3): į 2.61 (t, 4H, J = 4.5 Hz), 3.69–3.79 (m, 4H), 4.85 (s,
1H), 7.37–7.46 (m, 3H), 7.54–7.57 (m, 2H). 13C NMR (75
MHz, CDCl3): į 50.0, 62.46, 66.69, 115.18, 128.04, 128.87,
129.12, 132.46. Anal. Calcd for C12H14N2O: C, 71.26; H, 6.98;
N, 13.85; Found: C, 71.55; H, 7.25; N, 14.01.
(4-Chloro-phenylamino)-(3,4,5-trimethoxy-phenyl)-acetoni
trile (1g): white solid; recrystallized from ethanol; m.p.
145–148 oC. IR (KBr, cm–1): Ȟ 3380 (vs), 2950 (m), 2910 (s),
2807 (m), 2340 (m), 1590 (vs), 1500 (vs), 1458 (s), 1418 (s),
1338 (s), 1310 (s), 1279 (s), 1240 (s), 1230 (vs), 1180 (m),
1
1081 (m), 999 (s), 810 (s), 720 (s). H NMR (400 MHz,
CDCl3): į 3.87 (s, 3H), 3.88 (s, 6H), 4.12 (d, 1H, J = 8.4 Hz),
5.32 (d, 1H, J = 8.0 Hz), 6.72 (d, 2H, J = 8.8 Hz), 6.78 (s, 2H),
7.23–7.26 (m, 2H). 13C NMR (100 MHz, CDCl3): į 50.42,
56.23, 60.89, 104.22, 115.35, 117.97, 125.05, 128.94, 129.45,
138.64, 143.33, 153.77. Anal. Calcd for C17H17ClN2O3: C,
61.36; H, 5.15; N, 8.42; Found: C, 61.13; H, 5.12; N, 8.28.
(3-Nitro-phenyl)-phenylamino-acetonitrile (1h): pale yellow
(4-Methoxy-phenyl)-morpholin-4-yl-acetonitrile
(1m):
o
white solid; recystalized from ethanol; m.p. 72–74 C); IR
(KBr, cm–1): Ȟ 2925 (s), 2810 (s), 2320 (m), 1610 (m), 1585
(m), 1510 (vs), 1465 (s), 1418 (s), 1340 (s), 1320 (s), 1279 (s),
1250 (s), 1235 (vs), 1158 (s), 1140 (s), 1115 (vs), 1020 (s),
1
1000 (s), 865 (vs), 779 (s). H NMR (400 MHz, CDCl3): į
2.50–2.58 (m, 4H), 3.68–3.77 (m, 4H), 3.83 (s, 3H), 4.76 (s,
1H), 6.93 (d, 2H, J = 8.8 Hz), 7.44 (d, 2H, J = 4.8 Hz). 13C
NMR (100 MHz, CDCl3): į 49.88, 55.37, 61.82, 66.68, 114.14,
115.46, 124.44, 129.30, 160.09. Anal. Calcd for C13H16N2O2:
C, 67.22; H, 6.94; N, 12.06; Found: C, 66.98; H, 6.89; N,
11.92.
o
o
solid; recrystallized from ethanol; mp 88–91 C (89–92 C
[14]). IR (KBr, cm–1): Ȟ 3355 (s), 2870 (s), 2240 (m), 1598 (s),
1530 (vs), 1342 (s), 1092 (s), 902 (s), 785 (s), 744 (s), 690 (s).
1H NMR (300 MHz, CDCl3): į 4.19 (brs, 1H), 5.60 (s, 1H),
6.80 (d, 2H, J = 8.1 Hz), 6.97 (t, 1H, J = 7.7 Hz), 7.30 (m, 2H),
7.70 (t, 1H, J = 7.7 Hz), 8.01 (d, 1H, J = 8.1 Hz), 8.33 (d, 1H, J
= 8.7 Hz), 8.53 (s, 1H). 13C NMR (75 MHz, CDCl3): į 49.72,
114.66, 121.17, 122.40, 124.54, 129.75, 130.51, 133.04,
143.94. Anal. Calcd for C14H13N3O2: C, 66.40; H, 4.38; N,
(3,4-Dimethoxy-phenyl)-morpholin-4-yl-acetonitrile (1n):
o
white solid; recystalized from ethanol; m.p. 88–91 C); IR
(KBr, cm–1): Ȟ 2925 (s), 2810 (s), 2320 (m), 1610 (m), 1585
(m), 1510 (vs), 1465 (s), 1418 (s), 1340 (s), 1320 (s), 1279 (s),