Ethyl 2-((3-bromophenyl)(phenylamino)methyl)acrylate (3j).
(CDCl3, 75 MHz): 14.1, 55.7, 59.8, 60.8, 114.7, 114.8, 125.9,
127.5, 127.7, 128.7, 140.6, 141.0, 141.0, 152.3, 166.3;
ESI-HRMS m/z calcd for C19H22NO3 312.1594 (M+), found
312.1592.
Compound 3j was isolated as a yellow oil, IR νmax (KBr, cm−1):
1
3475, 2981, 1699, 1509; HNMR (CDCl3, 300 MHz): 1.23 (t,
3H, J = 7.2 Hz), 4.14–4.19 (m, 3H), 5.37 (d, 1H, J = 5.4 Hz),
5.92 (s, 1H), 6.41 (s, 1H), 6.57 (d, 2H, J = 7.8 Hz), 6.73 (t, 1H,
J = 7.5 Hz), 7.13–7.17 (m, 3H), 7.19 (d, 1H, J = 3.3 Hz), 7.23
(d, 1H, J = 5.4 Hz), 7.30 (s, 1H); 13C NMR (CDCl3, 75 MHz):
14.1, 58.6, 61.0, 113.5, 118.2, 122.8, 126.2, 126.7, 129.3, 130.3,
130.5, 130.9, 139.9, 143.1, 146.5, 165.9; ESI-HRMS m/z calcd
for C18H19BrNO2 360.0594 (M+), found 360.0588.
Ethyl 2-[((2-methoxyphenyl)amino)(phenyl)methyl]acrylate
(3p). Compound 3p was isolated as a yellow oil, IR νmax (KBr,
1
cm−1): 3417, 2960, 1715, 1509; HNMR (CDCl3, 300 MHz):
1.13 (t, 3H, J = 7.2 Hz), 3.74 (s, 3H), 3.97–4.15 (m, 2H), 4.61
(d, 1H, J = 5.1 Hz), 5.34 (d, 1H, J = 4.8 Hz), 5.83 (s, 1H), 6.31
(s, 1H), 6.43 (d, 1H, J = 7.8 Hz), 6.57–6.58 (m, 1H), 6.61 (d,
1H, J = 7.5 Hz), 6.69–6.77 (m, 2H), 7.20–7.32 (m, 5H); 13C
NMR (CDCl3, 75 MHz): 14.4, 55.7, 59.0, 61.1, 109.7, 111.3,
117.3, 121.4, 126.0, 128.0, 128.0, 129.0, 137.0, 140.8, 141.2,
147.1, 166.6; ESI-HRMS m/z calcd for C19H22NO3 312.1594
(M+), found 312.1591.
Ethyl 2-((2-bromophenyl)(phenylamino)methyl)acrylate (3k).
Compound 3k was isolated as a yellow oil, IR νmax (KBr, cm−1):
1
3522, 2981, 1711, 1503; HNMR (CDCl3, 300 MHz): 1.21 (t,
3H, J = 7.2 Hz), 4.07 (d, 1H, J = 5.7 Hz), 4.13–4.23 (m, 2H),
5.77 (s, 1H), 5.81 (d, 1H, J = 5.7 Hz), 6.44 (s, 1H), 6.56 (d, 2H,
J = 7.5 Hz), 6.72 (t, 1H, J = 7.2 Hz), 7.12–7.18 (m, 3H),
7.25–7.39 (m, 1H), 7.39–7.40 (m, 1H), 7.59–7.61 (m, 1H); 13C
NMR (CDCl3, 75 MHz): 14.1, 57.9, 61.0, 113.3, 118.0, 124.7,
127.4, 127.7, 128.5, 129.2, 129.2, 133.3, 139.6, 139.9, 146.6,
166.1; ESI-HRMS m/z calcd for C18H19BrNO2 360.0594 (M+),
found 360.0591.
Ethyl 2-((p-tolylamino)(phenyl)methyl)acrylate (3q). Com-
pound 3q was isolated as a yellow oil, IR νmax (KBr, cm−1):
1
3396, 2982, 1713, 1518; HNMR (CDCl3, 300 MHz): 1.20 (t,
3H, J = 7.2 Hz), 2.22 (s, 3H), 4.04 (br, 1H), 4.08–4.19 (m, 2H),
5.34 (s, 1H), 5.93 (s, 1H), 6.38 (s, 1H), 6.50 (d, 1H, J = 8.4 Hz),
6.97 (d, 1H, J = 8.4 Hz), 7.26–7.38 (m, 5H); 13C NMR (CDCl3,
75 MHz): 14.1, 20.4, 59.3, 60.8, 113.6, 125.9, 127.1, 127.6,
127.7, 128.7, 129.7, 140.5, 140.9, 144.5, 166.3; ESI-HRMS m/z
calcd for C19H22NO2 296.1645 (M+), found 296.1640.
Ethyl 2-[(naphthalen-2-yl)(phenylamino)methyl]acrylate (3l).
Compound 3l was isolated as a yellow oil, IR νmax (KBr, cm−1):
1
3407, 2980, 1711, 1502; HNMR (CDCl3, 300 MHz): 1.19 (t,
3H, J = 7.2 Hz), 4.09–4.17 (m, 2H), 4.24 (br, 1H), 5.58 (s, 1H),
5.99 (s, 1H), 6.44 (s, 1H), 6.61 (d, 2H, J = 7.8 Hz), 6.73 (t, 1H,
J = 7.5 Hz), 7.14–7.19 (m, 2H), 7.46–7.48 (m, 3H), 7.79–7.84
(m, 4H); 13C NMR (CDCl3, 75 MHz): 14.1, 59.1, 60.9, 113.5,
118.0, 125.8, 126.1, 126.2, 127.7, 128.1, 128.6, 129.2, 133.0,
133.4, 138.1, 140.4, 146.8, 166.3; ESI-HRMS m/z calcd for
C22H22NO2 332.1645 (M+), found 332.1641.
Ethyl 2-((o-tolylamino)(phenyl)methyl)acrylate (3r). Com-
pound 3r was isolated as a yellow oil, IR νmax (KBr, cm−1):
3412, 2981, 1712, 1510; HNMR (CDCl3, 300 MHz): 1.24 (t,
3H, J = 7.2 Hz), 2.18 (s, 3H), 4.08 (br, 1H), 4.11–4.24 (m, 2H),
5.50 (s, 1H), 5.93 (s, 1H), 6.41 (s, 1H), 6.54 (d, 1H, J = 7.8 Hz),
6.71 (d, 1H, J = 7.2 Hz), 7.08–7.13 (m, 2H), 7.28–7.33 (m, 4H);
13C NMR (CDCl3, 75 MHz): 14.4, 17.9, 59.2, 61.1, 111.3,
117.8, 122.5, 126.2, 127.3, 127.8, 129.1, 130.4, 140.7, 141.2,
145.0, 166.6; ESI-HRMS m/z calcd for C19H22NO2 296.1645
(M+), found 296.1641.
1
Ethyl 2-methylene-3-(phenylamino)pentanoate (3m). Com-
pound 3m was isolated as a yellow oil, IR νmax (KBr, cm−1):
1
3477, 2970, 1709, 1505; HNMR (CDCl3, 300 MHz): 1.00 (t,
3H, J = 7.2 Hz), 1.31 (t, 3H, J = 7.2 Hz), 1.58–1.87 (m, 2H),
4.03 (br, 1H), 4.18–4.27 (m, 3H), 5.71 (s, 1H), 6.20 (s, 1H),
6.54 (d, 2H, J = 7.8 Hz), 6.67 (t, 1H, J = 7.5 Hz), 7.14 (t, 1H,
J = 7.5 Hz); 13C NMR (CDCl3, 75 MHz): 10.9, 14.2, 28.5, 56.4,
60.7, 113.4, 117.4, 125.1, 129.2, 141.0, 147.1, 166.6;
ESI-HRMS m/z calcd for C14H20NO2 234.1489 (M+), found
234.1488.
Ethyl 2-[((4-fluorophenyl)amino)(phenyl)methyl]acrylate (3s).
Compound 3s was isolated as a yellow oil, IR νmax (KBr, cm−1):
3413, 2983, 1712, 1511; HNMR (CDCl3, 300 MHz): 1.20 (t,
3H, J = 7.2 Hz), 4.08–4.18 (m, 3H), 5.34 (s, 1H), 5.89 (s, 1H),
6.38 (s, 1H), 6.47–6.52 (m, 2H), 6.85 (t, 2H, J = 8.7 Hz),
7.27–7.32 (m, 5H); 13C NMR (CDCl3, 75 MHz): 14.1, 59.6,
60.9, 114.3, 114.4, 115.5, 115.8, 126.0, 127.5, 127.8, 128.5,
128.8, 129.3, 140.3, 140.6, 143.1, 143.1, 154.4, 157.6, 166.2;
ESI-HRMS m/z calcd for C18H19FNO2 300.1394 (M+), found
300.1391.
1
Ethyl 2-methylene-3-(phenylamino)hexanoate (3n). Com-
pound 3n was isolated as a yellow oil, IR νmax (KBr, cm−1):
1
3407, 2957, 1714, 1505; HNMR (CDCl3, 300 MHz): 0.94 (t,
3H, J = 7.2 Hz), 1.40–1.76 (m, 4H), 3.77 (s, 3H), 4.01 (br, 1H),
4.23–4.28 (m, 1H), 5.73 (s, 1H), 6.18 (s, 1H), 6.53 (d, 2H, J =
7.8 Hz), 6.67 (t, 1H, J = 7.5 Hz), 7.13 (t, 1H, J = 7.5 Hz); 13C
NMR (CDCl3, 75 MHz): 13.9, 19.7, 37.8, 51.8, 54.7, 113.4,
117.4, 125.3, 129.2, 141.1, 147.0, 167.0; ESI-HRMS m/z calcd
for C14H20NO2 234.1489 (M+), found 234.1486.
Ethyl 2-[((4-chlorophenyl)amino)(phenyl)methyl]acrylate (3t).
Compound 3t was isolated as a yellow oil, IR νmax (KBr, cm−1):
1
3413, 2982, 1712, 1497; HNMR (CDCl3, 300 MHz): 1.21 (t,
3H, J = 7.2 Hz), 4.10–4.20 (m, 3H), 5.34 (s, 1H), 5.88 (s, 1H),
6.38 (s, 1H), 6.49 (d, 2H, J = 8.7 Hz), 7.09 (d, 2H, J = 9.0 Hz),
7.28–7.34 (m, 5H); 13C NMR (CDCl3, 75 MHz): 14.1, 59.1,
60.9, 114.6, 122.5, 126.0, 127.5, 127.9, 128.5, 128.8, 129.0,
140.1, 140.3, 145.3, 166.1; ESI-HRMS m/z calcd for
C18H19ClNO2 316.1099 (M+), found 316.1093.
Ethyl 2-[((4-methoxyphenyl)amino)(phenyl)methyl]acrylate
(3o). Compound 3o was isolated as a yellow oil, IR νmax (KBr,
1
cm−1): 3438, 2930, 1712, 1512; HNMR (CDCl3, 300 MHz):
1.18–1.26 (m, 3H), 3.72 (s, 3H), 4.00 (br, 1H), 4.12–4.15 (m,
2H), 5.33 (s, 1H), 5.92 (s, 1H), 6.37 (s, 1H), 6.53 (d, 2H, J = 8.7
Hz), 6.75 (d, 2H, J = 8.7 Hz), 7.24–7.38 (m, 5H); 13C NMR
Ethyl 2-[((3-chlorophenyl)amino)(phenyl)methyl]acrylate (3u).
Compound 3u was isolated as a yellow oil, IR νmax (KBr, cm−1):
6912 | Org. Biomol. Chem., 2012, 10, 6908–6913
This journal is © The Royal Society of Chemistry 2012