# 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): 168.7 (COOH), 149.5 (C), 145.4 (CH), 130.3 (CH), 121.4 (C), 112.7 (CH), 112.1 (CH), 47.7 (NCH\({}_{2}\)), 25.4 (CH\({}_{2}\)). IR (KBr): 1673, 1588, 1526, 1391, 1261, 1179, 815. Anal. Calcd for C\({}_{13}\)H\({}_{15}\)NO\({}_{2}\): C, 71.87; H, 6.96; N, 6.45. Found: C, 71.88; H, 6.87; N, 6.40. 3-[4-(Pyrrolidin-1-yl)phenyl)acrylic acid (2i)  
The compound was obtained as a pale-yellow solid; yield: 72%; mp 223 \({}^{\circ}\)C.  
\({}^{1}\)H NMR (400 MHz, DMSO-\(d_{6}\)) \(\sigma\) (ppm): 12.03 (s, 1H, COOH), 7.50-7.45 (m, 3H), 6.91 (d, \(J\) = 9.0 Hz, 2H), 6.25 (d, \(J\) = 15.8 Hz, 1H, -CH=), 3.26 (t, \(J\) = 5.0 Hz, 4H, NCH\({}_{2}\)), 1.58 (m, 6H). \({}^{13}\)C NMR (100 MHz, DMSO-\(d_{6}\)) \(\sigma\) (ppm): 168.6 (COOH), 152.8 (C), 144.7 (CH), 130.1 (CH), 123.7 (C), 114.9 (CH), 114.4 (CH), 48.7 (NCH\({}_{2}\)), 25.4 (CH\({}_{2}\)), 24.4 (CH\({}_{2}\)). IR (KBr): 1666, 1602, 1519, 1241, 1188, 1126, 817. Anal. Calcd for C\({}_{14}\)H\({}_{17}\)NO\({}_{2}\): C, 72.71; H, 7.41; N, 6.06. Found: C, 72.72; H, 7.30; N, 6.03. 3-[4-(Morpholin-4-yl)phenyl)acrylic acid (2j)The compound was obtained as a pink solid; yield: 88%; mp 247 \({}^{\circ}\)C.  
\({}^{1}\)H NMR (400 MHz, DMSO-\(d_{6}\)) \(\sigma\) (ppm): 12.09 (s, 1H, COOH), 7.54-7.38 (m, 3H), 6.95 (d, \(J\) = 8.9 Hz, 2H), 6.30 (d, \(J\) = 15.9 Hz, 1H, -CH=), 3.74 (t, \(J\) = 4.9 Hz, 4H, NCH\({}_{2}\)), 3.21 (t, \(J\) = 4.9 Hz, 4H, OCH\({}_{2}\)). \({}^{13}\)C NMR (100 MHz, DMSO-\(d_{6}\)) \(\sigma\) (ppm): 168.5 (COOH), 152.8 (C), 144.6 (CH), 130.0 (CH), 124.9 (C), 115.2 (CH), 114.7 (CH), 66.4 (OCH\({}_{2}\)), 47.8 (NCH\({}_{2}\)). IR (KBr): 1704, 1604, 1517, 1174, 1112, 820, 618. Anal. Calcd for C\({}_{13}\)H\({}_{15}\)NO\({}_{3}\) C, 66.94; H, 6.48; N, 6.01. Found: C, 67.02; H, 6.36; N, 6.09. 3-(1-Methyl-2,3-dihydro-1H-indol-5-yl)acrylic acid (2k)  
The compound was obtained as a brown solid; yield: 58%; mp 15 \({}^{\circ}\)C.  
\({}^{1}\)H NMR (400 MHz, DMSO-\(d_{6}\)) \(\sigma\) (ppm): 11.93 (s, 1H, COOH), 7.45 (d, \(J\) = 15.8 Hz, 1H, -CH=), 7.37 (s, 1H), 7.29 (d, \(J\) = 8.1 Hz, 1H), 6.46 (d, \(J\) = 8.1 Hz, 1H), 6.17 (d, \(J\) = 15.8 Hz, 1H, -CH=), 3.38 (t, \(J\) = 8.2 Hz, 2H, NCH\({}_{2}\)), 2.91 (t, \(J\) = 8.3 Hz, 2H ArCH\({}_{2}\)), 2.77 (s, 3H, NCH\({}_{3}\)). \({}^{13}\)C NMR (100 MHz, DMSO-\(d_{6}\)) \(\sigma\) (ppm): 168.8 (COOH), 155.6 (C), 145.4 (CH), 131.1 (C), 130.5 (CH), 123.7 (CH), 123.6 (C), 113.2 (CH), 106.3 (CH), 55.3 (NCH\({}_{2}\)), 35.1 (NCH\({}_{3}\)), 27.9 (ArCH\({}_{2}\)). IR (KBr): 1676, 1592, 1517, 1294, 1230, 1201. Anal. Calcd for C\({}_{12}\)H\({}_{13}\)NO\({}_{2}\): C, 70.92; H, 6.45; N, 6.89. Found: C, 70.84; H, 6.41; N, 6.82. 3-(1-Methyl-1,2,3,4- tetrahydroduvinolin-6-yl)acrylic acid (2l)  
The compound was obtained as a brown solid; yield: 65%; mp 158 \({}^{\circ}\)C.  
\({}^{1}\)H NMR (400 MHz, DMSO-\(d_{6}\)) \(\sigma\) (ppm): 11.92 (s, 1H, COOH), 7.41 (d, \(J\) = 15.8 Hz, 1H, -CH=), 7.28 (d, \(J\) = 8.5 Hz, 1H), 7.22 (s, 1H), 6.54 (d, \(J\) = 8.6 Hz, 1H), 6.15 (d, \(J\) = 16.1 Hz, 1H, -CH=), 3.28 (t, \(J\) = 5.7 Hz, 2H, NCH\({}_{2}\)), 2.90 (s, 3H, NCH\({}_{3}\)), 2.69 (t, \(J\) = 6.2 Hz, 2H, ArCH\({}_{2}\)), 1.87 (m, 2H). \({}^{13}\)C NMR (100 MHz, DMSO-\(d_{6}\)) \(\sigma\) (ppm): 168.7 (COOH), 148.6 (C), 145.3 (CH), 129.0 (CH), 128.8 (CH), 122.5 (CH), 121.7 (CH), 110.6 (CH), 50.9 (NCH\({}_{2}\)), 38.9 (NCH\({}_{3}\)), 27.6 (ArCH\({}_{2}\)), 21.9 (CH\({}_{2}\)). IR (KBr): 1672, 1658, 1599, 1522, 1321, 1269, 1206. Anal. Calcd for C\({}_{13}\)H\({}_{15}\)NO\({}_{2}\): C, 71.87; H, 6.96; N, 6.45. Found: C, 71.81; H, 6.87; N, 6.38. 3-(9-Julolidyl)acrylic acid (2m)  
The compound was obtained as a light-brown solid; yield: 64%; mp 178 \({}^{\circ}\)C.  
\({}^{1}\)H NMR (400 MHz, DMSO-\(d_{6}\)) \(\sigma\) (ppm): 11.86 (s, 1H, COOH), 7.34 (d, \(J\) = 15.8 Hz, 1H, -CH=), 7.01 (s, 2H), 6.08 (d, \(J\) = 15.7 Hz, 1H, -CH=), 3.19 (t, \(J\) = 5.7 Hz, 4H, NCH\({}_{2}\)), 2.66 (t, \(J\) = 6.3 Hz, 4H, ArCH\({}_{2}\)), 1.85 (m, 4H, CH\({}_{2}\)).