# Aromatic Amines in Organic Synthesis Part III; \(p\)-Aminocinnamic Acids and Their Methyl Esters
## 3 Materials and Methods
### Synthesis
#### 3.1.2 Synthesis of the Methyl \(p\)-(Dimethylamino)cinnamate
\({}^{13}\)C NMR (100 MHz, DMSO-\(d_{6}\)) \(\sigma\) (ppm): 168.8 (COOH), 145.4 (CH), 144.9 (C), 127.7 (CH), 120.94 (C), 120.90 (C), 112.2 (CH), 49.6 (CH\({}_{2}\)), 27.5 (CH\({}_{2}\)), 21.6 (CH\({}_{2}\)). IR (KBr): 1653, 1592, 1513, 1312, 1256, 1160. Anal. Calcd for C\({}_{15}\)H\({}_{17}\)NO\({}_{2}\): C, 74.05; H, 7.04; N, 5.76. Found: C, 73.98; H, 6.97; N, 5.72. 3-[4-(Dimethylamino)napththalen-1-yl]acrylic acid (2n)  
The compound was obtained as a yellow solid; yield: 61%; mp 166 \({}^{\circ}\)C.  
\({}^{1}\)H NMR (400 MHz, DMSO-\(d_{6}\)) \(\sigma\) (ppm): 12.42 (s, 1H, COOH), 8.33 (d, \(J\) = 15.7 Hz, 1H, -CH=), 8.20-8.17 (m, 2H), 7.90 (d, \(J\) = 8 Hz, 1H), 7.63-7.55 (m, 2H), 7.12 (d, \(J\) = 8 Hz, 1H), 6.50 (d, \(J\) = 15.6 Hz, 1H, -CH=), 2.88 (s, 6H, N(CH\({}_{3}\))\({}_{2}\)). \({}^{13}\)C NMR (100 MHz, DMSO-\(d_{6}\)) \(\sigma\) (ppm): 168.2 (COOH), 153.2 (C), 140.7 (CH), 132.7 (C), 128.1 (C), 127.4 (CH), 126.3 (CH), 125.7 (CH), 125.3 (CH), 125.2 (C), 123.8 (CH), 119.7 (CH), 114.0 (C), 45.0 (N(CH\({}_{3}\))\({}_{2}\)). IR (KBr): 1676, 1611, 1570, 1417, 1338, 1212, 770. Anal. Calcd for C\({}_{15}\)H\({}_{15}\)NO\({}_{2}\): C, 74.67; H, 6.27; N, 5.81. Found: C, 74.51; H, 6.32; N, 5.88. 3-[6-(Dimethylamino)napththalen-2-yl]acrylic acid (2o)  
The compound was obtained as a yellow solid; yield: 63%; mp 251 \({}^{\circ}\)C.  
\({}^{1}\)H NMR (400 MHz, DMSO-\(d_{6}\)) \(\sigma\) (ppm): 12.16 (s, 1H, COOH), 7.94 (s, 1H), 7.76 (d, \(J\) = 9.1 Hz, 1H), 7.69-7.62 (m, 3H), 7.24 (d, \(J\) = 9.1 Hz, 1H), 6.95 (s, 1H), 6.50 (d, \(J\) = 15.9 Hz, 1H, -CH=), 3.04 (s, 6H, N(CH\({}_{3}\))\({}_{2}\)). \({}^{13}\)C NMR (100 MHz, DMSO-\(d_{6}\)) \(\sigma\) (ppm): 168.5 (COOH), 149.7 (C), 144.7 (CH), 136.2 (C), 130.2 (CH), 129.9 (CH), 128.0 (C), 127.0 (CH), 126.0 (C), 124.6 (CH), 117.5 (CH), 116.9 (CH), 105.8 (CH), 40.5 (N(CH\({}_{3}\))\({}_{2}\)). IR (KBr): 1683, 1612, 1599, 1428, 1312, 1202, 1176, 842. Anal. Calcd for C\({}_{15}\)H\({}_{15}\)NO\({}_{2}\): C, 74.67; H, 6.27; N, 5.81. Found: C, 74.58; H, 6.39; N, 5.84. _Methyl 3-[4-(dimethylamino)phenyl]acrylate (3a)_  
The compound was obtained as a pale-yellow solid; yield: 73% (method B), 76% (method C), 82% (method D); mp 137  
The compound was obtained as a yellow solid; yield: 71% (method B), 72% (method C), 83% (method D); mp 146 \({}^{\circ}\)C.  
\({}^{1}\)H NMR (400 MHz, DMSO-\(d_{6}\)) \(\sigma\) (ppm): 7.56-7.50 (m, 3H), 6.54 (d, \(J\) = 8.8 Hz, 2H), 6.28 (d, \(J\) = 15.8 Hz, 1H, -CH=), 3.67 (s, 3H, OCH\({}_{3}\)), 3.28 (t, \(J\) = 6.5 Hz, 4H, NCH\({}_{2}\)), 1.96 (m, 4H, CH\({}_{2}\)). \({}^{13}\)C NMR (100 MHz, DMSO-\(d_{6}\)) \(\sigma\) (ppm): 167.8 (COO), 149.7 (C), 145.9 (CH), 130.6 (CH), 121.2 (C), 112.1 (CH), 111.2 (CH), 51.5 (OCH\({}_{3}\)), 47.7 (NCH\({}_{2}\)), 25.4 (CH\({}_{2}\)). IR (KBr): 1708, 1701, 1605, 1527, 1393, 1184, 1164, 985, 814. Anal. Calcd for C\({}_{14}\)H\({}_{17}\)NO\({}_{2}\): C, 72.71; H, 7.41; N, 6.06. Found: C, 72.65; H, 7.38; N, 6.01. _Methyl 3-[4-(piperidin-1-yl)phenyl]acrylate (3i)_  
The compound was obtained as a light-pink-yellow solid; yield: 84% (method B), 81% (method C), 93% (method D); mp 101 \({}^{\circ}\)C.  
\({}^{1}\)H NMR (400 MHz, DMSO-\(d_{6}\)) \(\sigma\) (ppm): 7.56-7.51 (m, 3H), 6.91 (d, \(J\) = 8.9 Hz, 2H), 6.35 (d, \(J\) = 15.9 Hz, 1H, -CH=), 3.68 (s, 3H, OCH\({}_{3}\)), 3.29 (t, \(J\) = 5.0 Hz, 4H, NCH\({}_{2}\)), 1.57 (m, 6H). \({}^{13}\)C NMR (100 MHz, DMSO-\(d_{6}\)) \(\sigma\) (ppm): 167.7 (COO), 153.0 (C), 145.2 (CH), 130.4 (CH), 123.4 (C), 114.8 (CH), 112.9 (CH), 51.6 (OCH\({}_{3}\)), 48.7 (NCH\({}_{2}\)), 25.4 (CH\({}_{2}\)), 24.4 (CH\({}_{2}\)); IR (KBr): 1708, 1625, 1604, 1518, 1190, 1170, 1127, 985, 816. Anal. Calcd for C\({}_{15}\)H\({}_{19}\)NO\({}_{2}\): C, 73.45; H, 7.81; N, 5.71. Found: C, 73.37; H, 7.75; N, 5.77.