Med Chem Res (2011) 20:1273–1279
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Calcd. for C13H17N1O4: C, 62.14; H, 6.82; N, 5.57. Found:
C, 65.24; H, 6.90; N, 5.51.
Anal. Calcd. for C12H15N1O4: C, 60.75; H, 6.37; N, 5.90.
Found: C, 60.91; H, 6.44; N, 5.76.
(E)-3-(4-fluorophenyl)-N-(2-hydroxyethyl)acrylamide (1j)
(E)-N-(2-hydroxyethyl)-3-(3,4,
5-trimethoxyphenyl)acrylamide (1f)
1
Yield: 56.1%; mp 90–92°C. H-NMR (CDCl3, 300 MHz):
d 2.19 (s, 1H, –OH), 3.56 (q, 2H, J = 5.3 Hz, –CH2), 3.80
(t, 2H, J = 4.7 Hz, –CH2), 6.25 (s, 1H, –NHCO), 6.35 (d,
1H, J = 15.6 Hz, CH=C), 6.77 (d, 2H, J = 8.2 Hz, Ar–H),
7.30 (d, 1H, J = 15.7 Hz, CH=C), 7.37 (d, 2H,
J = 8.2 Hz, Ar–H). IR (KBr) cm-1: 3332 (OH), 3220
(NH), 1640 (C=O). MS (m/z): 210 (M ? 1). Anal. Calcd.
for C11H13N1O3: C, 63.15; H, 5.78; N, 6.69. Found: C,
63.34; H, 5.85; N, 6.78.
Yield: 46.3%; mp 120–122°C. 1H-NMR (CDCl3,
300 MHz): d 2.55 (s, 1H, -OH), 3.57 (q, 2H, J = 4.8 Hz,
–CH2), 3.80 (t, 2H, J = 4.7 Hz, –CH2), 3.84 (s, 9H,
–OCH3, –OCH3, –OCH3), 6.33 (s, 1H, –NHCO), 6.35 (d,
1H, J = 15.5 Hz, CH=C), 6.71 (s, 2H, Ar–H), 7.54 (d, 1H,
J = 15.5 Hz, CH=C). IR (KBr) cm-1: 3405 (OH), 3266
(NH), 1620 (C=O). MS (m/z): 282 (M ? 1). Anal. Calcd.
for C14H19N1O5: C, 59.78; H, 6.81; N, 4.98. Found: C,
59.93; H, 6.80; N, 5.06.
(E)-3-(4-chlorophenyl)-N-(2-hydroxyethyl)acrylamide (1k)
N-(2-hydroxyethyl)cinnamamide (1g)
Yield: 63.6%; mp 130–132°C. 1H-NMR (CDCl3,
300 MHz): d 2.28 (s, 1H, –OH), 3.58 (q, 2H, J = 5.3 Hz,
–CH2), 3.82 (t, 2H, J = 4.8 Hz, –CH2), 6.22 (d, 1H,
J = 15.7 Hz, CH=C), 6.30 (s, 1H, –NHCO), 6.89 (d, 2H,
J = 8.2 Hz, Ar–H), 7.36 (d, 1H, J = 15.7 Hz, CH=C),
7.42 (d, 2H, J = 8.2 Hz, Ar–H). IR (KBr) cm-1: 3339
(OH), 3218 (NH), 1644 (C=O). MS (m/z): 226 (M ? 1).
Anal. Calcd. for C11H13N1O3: C, 58.54; H, 5.36; N, 6.21.
Found: C, 58.71; H, 5.44; N, 6.08.
Yield: 52.7%; mp 100–102°C. 1H-NMR (CDCl3,
300 MHz): d 2.61(s, 1H, –OH), 3.56 (q, 2H, J = 5.0 Hz,
–CH2), 3.80 (t, 2H, J = 4.8 Hz, –CH2), 6.42 (s, 1H,
–NHCO), 6.44 (d, 1H, J = 15.7 Hz, CH=C), 7.36–7.47 (m,
5H, Ar–H), 7.69(d, 1H, J = 15.7 Hz, CH=C). IR (KBr)
cm-1: 3389 (OH), 3215 (NH), 1661 (C=O). MS (m/z): 192
(M ? 1). Anal. Calcd. for C11H13NO2: C, 69.09; H, 6.85;
N, 7.32. Found: C, 69.20; H, 6.92; N, 7.39.
(E)-3-(4-bromophenyl)-N-(2-hydroxyethyl)acrylamide (1l)
(E)-3-(4-(dimethylamino)phenyl)-N-
(2-hydroxyethyl)acrylamide (1h)
Yield: 59.3%; mp 142–144°C. 1H-NMR (CDCl3,
300 MHz): d 1.61 (s, 1H, –OH), 3.57 (s, 1H, –CH2), 3.82
(t, 2H, J = 4.7 Hz, –CH2), 6.13 (s, 1H, –NHCO), 6.44 (d,
1H, J = 16.0 Hz, CH=C), 7.39 (d, 2H, J = 8.3 Hz, Ar–H),
7.53 (d, 2H, J = 8.3 Hz, Ar–H), 7.63 (d, 1H, J = 16.0 Hz,
CH=C). IR (KBr) cm-1: 3342 (OH), 3266 (NH), 1638
(C=O). MS (m/z): 271 (M ? 1). Anal. Calcd. for
C11H12N1O3Br: C, 48.91; H, 4.48; N, 5.19. Found: C,
49.09; H, 4.40; N, 5.04.
Yield: 43.8%; mp 110–112°C. 1H-NMR (CDCl3,
300 MHz): d 2.77 (s, 1H, –OH), 3.01 (s, 6H, –(NH3)2),
3.56 (q, 2H, J = 5.3 Hz, –CH2), 3.79 (t, 2H, J = 4.7 Hz,
–CH2), 5.98 (s, 1H, –NHCO), 6.21 (d, 1H, J = 15.4 Hz,
CH=C), 6.68 (d, 2H, J = 8.4 Hz, Ar–H), 7.40 (d, 2H,
J = 8.4 Hz, Ar–H), 7.58 (d, 1H, J = 15.4 Hz, CH=C). IR
(KBr) cm-1: 3356 (OH), 3228 (NH), 1647 (C=O). MS (m/z):
235 (M ? 1). Anal. Calcd. for C13H18N2O2: C, 66.64; H,
7.74; N, 11.96. Found: C, 66.77; H, 7.79; N, 11.85.
(E)-N-(2-hydroxyethyl)-3-(2-hydroxyphenyl)acrylamide
(1m)
(E)-3-(4-hydroxy-3-methoxyphenyl)-N-
(2-hydroxyethyl)acrylamide (1i)
Yield: 49.7%; mp 152–154°C. 1H-NMR (DMSO-d6,
300 MHz): d 3.23 (q, 2H, J = 5.7 Hz, –CH2), 3.41 (t, 2H,
J = 5.7 Hz, –CH2), 4.83 (s, 1H, –OH), 6.65 (d, 1H,
J = 15.9 Hz, CH=C), 6.80 (t, 1H, J = 7.4 Hz, Ar–H), 6.86
(d, 1H, J = 8.1 Hz, Ar–H), 7.16 (t, 1H, J = 6.8 Hz, Ar–
H), 7.41 (d, 1H, J = 7.2 Hz, Ar–H), 7.62 (d, 1H,
J = 15.9 Hz, CH=C), 8.09 (s, 1H, –NHCO), 10.1 (s, 1H,
Ar–OH). IR (KBr) cm-1: 3345 (OH), 3229 (NH), 1648
(C=O). MS (m/z): 208 (M ? 1). Anal. Calcd. for
Yield: 69.6%; mp 114–116°C. 1H-NMR (DMSO-d6,
300 MHz): d 3.23 (q, 2H, J = 5.8 Hz, –CH2), 3.44 (t, 2H,
J = 4.5 Hz, –CH2), 3.79 (s, 3H, –CH3), 4.71 (s, 1H, –OH),
6.49 (d, 1H, J = 15.7 Hz, CH=C), 6.78 (d, 1H,
J = 8.1 Hz, Ar–H), 6.94 (d, 1H, J = 8.1 Hz, Ar–H), 7.10
(s, 1H, Ar–H), 7.31 (d, 1H, J = 15.7 Hz, CH=C), 7.94 (s,
1H, –NHCO), 9.37 (s, 1H, Ar–OH). IR (KBr) cm-1: 3376
(OH), 3222 (NH), 1632 (C=O). MS (m/z): 238 (M ? 1).
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