The Selected Spectral Data for Amidoalkyl Naphthol Derivatives

Synthesis of amidoalkyl naphthol via Ritter-type reaction catalyzed by heteropolyanions-based ionic liquid

Fang Dong, Jiang Chenning, Cao Yanfang, Yang Jinming

Supporting information:

The selected spectral, analytical data for heteropoly anions-based Ionic liquid ([MIMPS]H2PMo12O40)

[MIMPS]H2PMo12O40 1H NMR (300 Mz, D2O): δppm 2.03 (m, J=7.2Hz, 2H, CH2), 2.64 (t, J=7.5Hz, 2H, CH2), 3.62 (s, 3H, CH3), 4.08 (t, J=6.9Hz, 2H, CH2), 7.17 (d, J=1.5Hz, 1H, CH), 7.24 (d, J=1.5Hz, 1H, CH), 8.47 (s, 1H, CH). 13C NMR (75 Mz, D2O): δppm 25.48, 36.46, 47.66, 48.13, 122.57, 124.32, 136.53. Anal. Calcd for C7H15N2O43SPMo12: C, 4.14; H, 0.75; N, 1.38. Found: C, 4.28; H, 0.79; N, 1.40.

The selected spectral, analytical data for amidoalkyl naphthol derivatives

N-((2-hydroxy-napthalen-1-yl)-phenylmethyl)-acetamide (Table 4, entry 1) White solid, mp 236-238 ℃; IR(KRr) 3400, 3249, 3062, 1639, 1581, 1514, 1436, 1373, 1336, 1278, 1209, 1166, 1060, 1027, 987, 933, 877, 838, 808, 742 cm-1. 1H NMR (300 MHz, DMSO-d6), δ: 1.98 (s, 3H), 7.17-7.36 (m, 9H), 7.77 -7.82 (m, 3H), 8.43-8.46 (d, 1H), 10.02 (s, 1H). 13C NMR (75 MHz, DMSO-d6): 23.3, 40.1, 119.3, 119.5, 122.2, 123.6, 126.5, 126.7, 128.4, 128.6, 128.9, 129.1, 129.4, 132.6, 143.3, 153.6, 168.5

N-((2-chloro-phenyl)-(2-hydroxy-napthalen-1-yl)-methyl)-acetamide (Table 4, entry 2) White solid, mp 193-195 ℃; IR(KRr) 3429, 3062, 3002, 1649, 1577, 1514, 1438, 1371, 1296, 1162, 1062, 810cm-1. 1H NMR (300 MHz, DMSO-d6), δ: 1.98 (s, 3H), 7.04-7.55 (m, 8H), 7.72-7.98 (m, 3H), 8.55-8.58 (d, 1H), 9.82 (s, 1H).

N-((4-chloro-phenyl)-(2-hydroxy-napthalen-1-yl)-methyl)-acetamide (Table 4, entry 3) White solid, mp 224-226 ℃; IR(KRr) 3420, 3060, 3005, 1645, 1575, 1510, 1438, 1370, 1298, 1162, 1065, 812cm-1. 1H NMR (300 MHz, DMSO-d6), δ: 1.99 (s, 3H), 7.03-7.57 (m, 8H), 7.71-7.92 (m, 3H), 8.55-8.59 (d, 1H), 9.89 (s, 1H).

N-((2,4-dichloro-phenyl)-(2-hydroxy-napthalen-1-yl)-methyl)-acetamide (Table 4, entry 4) White solid, mp 200-202 ℃; IR(KRr) 3419, 2066, 1637, 1583, 1515, 1469, 1440, 1371, 1338, 1267, 1251, 1105, 1064, 819, 740, 661cm-1. 1H NMR (300 MHz, DMSO-d6), δ: 1.92 (s, 1H), 6.98-7.58 (m, 7H), 7.73-7.95 (m, 3H), 8.64 (d, 1H), 9.84 (s, 1H).

N-((2-nitro-phenyl)-(2-hydroxy-napthalen-1-yl)-methyl)-acetamide (Table 4, entry 5) Yellow solid, mp 215-217 ℃; IR(KRr) 3405, 3098, 3036, 1648, 1577, 1544, 1436, 1360, 1288, 1166, 1062, 806cm-1. 1H NMR (300 MHz, DMSO-d6), δ: 2.01 (s, 3H), 7.16-7.58 (m, 8H), 7.79-8.08 (m, 3H), 8.55-8.65 (d, 1H), 9.82 (s, 1H).

N-((3-nitro-phenyl)-(2-hydroxy-napthalen-1-yl)-methyl)-acetamide (Table 4, entry 6) Yellow solid, mp 239-241 ℃; IR(KRr) 3375, 3195, 3089, 1647, 1577, 1525, 1436, 1350, 1257, 1166, 1060, 806cm-1. 1H NMR (300 MHz, DMSO-d6), δ: 2.02 (s, 3H), 7.17-7.57 (m, 8H), 7.79-8.06 (m, 3H), 8.55-8.65 (d, 1H), 10.16 (s, 1H).

N-((4-nitro-phenyl)-(2-hydroxy-napthalen-1-yl)-methyl)-acetamide (Table 4, entry 7) Yellow solid, mp 234-236 ℃; IR(KRr) 3415, 3185, 3076, 1637, 1589, 1515, 1436, 1364, 1265, 1168, 1062, 816cm-1. 1H NMR (300 MHz, DMSO-d6), δ: 2.02 (s, 3H), 7.19-7.60 (m, 8H), 7.80-8.06 (m, 3H), 8.57-8.60 (d, 1H), 10.15(s, 1H). 13C NMR (125 MHz, DMSO-d6): 22.5, 47.6, 117.7, 118.4, 120.3, 121.1, 122.5, 126.6, 128.3, 129.4, 129.8, 132.1, 132.7, 145.3, 147.7, 153.2, 169.5.

N-((4-methy-phenyl)-(2-hydroxy-napthalen-1-yl)-methyl)-acetamide (Table 4, entry 8) White solid, mp 218-220 ℃; IR(KRr) 3410, 3174, 3069, 1643, 1582, 1517, 1436, 1369, 1265, 1165, 1060, 810cm-1. 1H NMR (300 MHz, DMSO-d6), δ: 1.93 (s, 3H), 2.20 (s, 3H), 6.62-6.95 (m, 8H), 7.18-7.79 (m, 3H), 8.36-8.38 (d, 1H), 9.91(s, 1H). 13C NMR (75 MHz, DMSO-d6): δ: 20.4, 22.6, 47.6, 118.4, 118.9, 122.2, 123.1, 125.9, 126.1, 128.3, 128.4, 128.9, 132.2, 134.9, 139.4, 143.2, 152.9, 168.9.

N-((2-hydroxy-napthalen-1-yl)- phenylmethyl)benzamide (Table 4, entry 9) White solid, mp 232-234 ℃; IR(KRr) 3419, 3060, 3022, 1629, 1571, 1515, 1450, 1434, 1394, 1270, 1257, 1242, 1076, 943, 823, 696, 582cm-1. 1H NMR (300 MHz, DMSO-d6), δ: 3.41 (d, 1H), 7.21-7.34 (m, 8H), 7.49-7.56(m, 4H), 7.80-7.90(m, 4H), 8.11-8.13 (d, 1H), 9.04 (s, 1H).

N-((2-chloro-phenyl)-(2-hydroxy-napthalen-1-yl)-methyl)benzamide (Table 4, entry 10) White solid, mp 252-254 ℃; IR(KRr) 3400, 3051, 3017, 1628, 1577, 1513, 1460, 1439, 1386, 1260, 1257, 1238, 1076, 945, 822, 696, 582cm-1. 1H NMR (300 MHz, DMSO-d6), δ: 3.42 (d, 1H), 7.22-7.35 (m, 7H), 7.49-7.55(m, 4H), 7.79-7.91(m, 4H), 8.10-8.12 (d, 1H), 9.02 (s, 1H).

N-((3-nitro-phenyl)-(2-hydroxy-napthalen-1-yl)-methyl)benzamide (Table 4, entry 11) Yellow solid, mp 212-214 ℃; IR(KRr) 3412, 3046, 3020, 1631, 1577, 1521, 1461, 1438, 1387, 1260, 1254, 1238, 1075, 945, 820, 695, 580cm-1. 1H NMR (300 MHz, DMSO-d6), δ: 7.05 (d, 1H), 7.25-7.38 (m, 8H), 7.49-7.55(m, 4H), 7.81-8.06(m, 3H), 8.13-8.16 (d, 1H), 9.07 (s, 1H). 13C NMR (75 MHz, DMSO-d6), δ: 49.4, 117.3, 119.1, 121.5, 122.1, 122.7, 123.8, 127.5, 127.8, 128.7, 128.9, 129.2, 130.2, 130.5, 132.1, 132.9, 133.8, 134.5, 145.0, 148.0, 153.8, 166.7.

N-((4-nitro-phenyl)-(2-hydroxy-napthalen-1-yl)-methyl)benzamide (Table 4, entry 12) Yellow solid, mp 232-234 ℃; IR(KRr) 3423, 3046, 3017, 1630, 1577, 1520, 1463, 1430, 1381, 1260, 1250, 1238, 1075, 945, 821, 695, 580cm-1. 1H NMR (300 MHz, DMSO-d6), δ: 3.45 (d, 1H), 7.28-7.39 (m, 8H), 7.50-7.57(m, 4H), 7.83-8.05(m, 3H), 8.14-8.17 (d, 1H), 9.08 (s, 1H).

N-((4-methy-phenyl)-(2-hydroxy-napthalen-1-yl)-methyl)benzamide (Table 4, entry 13) Yellow solid, mp 212-214 ℃; IR(KRr) 3412, 3046, 3020, 1631, 1577, 1521, 1461, 1438, 1387 1260, 1254, 1238, 1075, 945, 820, 695, 580cm-1. 1H NMR (300 MHz, DMSO-d6), δ: 3.41 (d, 1H), 3.67 (s, 3H), 7.20-7.31 (m, 8H), 7.34-7.58(m, 4H), 7.72-7.89 (m, 3H), 8.09-8.12 (d, 1H), 9.07 (s, 1H).

N-((2-chloro-phenyl)-(2-hydroxynaphalen-1-yl)-methyl)-acrylamide (Table 4, entry 14) White solid, mp 220-222 ℃; IR(KRr) 3419, 3060, 3022, 1629, 1571, 1515, 1450, 1434, 1394, 1270, 1257, 1242, 1076, 943, 823, 696, 582cm-1. 1H NMR（300 MHz, DMSO-d6）δ: 5.56-5.60 (m, 2H), 6.09-6.12 (d, 1H), 6.49-6.55 (m,1H), 7.14-7.47 (m, 7H), 7.74-7.99 (m, 3H), 8.84-8.87 (d, 1H), 9.89 (s, 1H). 13C NMR（75 MHz, DMSO-d6）δ: 167.0, 153.5, 143.4, 133.6, 133.5, 131.1, 129.7, 129.4, 129.0, 128.8, 128.3, 128.2, 127.7, 127.4, 126.3, 123.2, 122.5, 118.9, 115.4, 40.1. MS: m/z=338 (M+). Anal. Calcd for C20H16NO2Cl: C, 71.11; H, 4.77; N, 4.15. Found: C, 71.32; H, 4.78; N, 4.27.

N-((4-methoxy-phenyl)-(2-hydroxynaphalen-1-yl)-methyl)-acrylamide (Table 4, entry 15) White solid, mp 218-220 ℃; IR(KRr) 3396, 3002, 2835, 1654, 1438, 1402, 1336, 1270, 1245, 1172, 1066, 966, 927, 850, 817, 750, 653, 597 cm-1. 1H NMR (300 MHz，DMSO-d6), 3.68 (s, 3H), δ: 5.62-5.68 (m, 2H), 6.11-6.14 (d, 1H), 6.81-7.37 (m, 8H), 7.75-7.85 (m, 3H), 8.70-8.72 (d, 1H), 10.03 (s, 1H).

N-((3-nitro-phenyl)-(2-hydroxy-napthalen-1-yl)-methyl)urea (Table 4, entry 16) White solid, mp 176-178 ℃; IR (KBr) 3420, 3393, 3193, 2925, 2849, 1726, 1655, 1601, 1527, 1476, 1439, 1350, 1315, 1267, 1206, 1142, 1095, 1040, 926, 812 cm-1. 1H NMR (300 MHz, DMSO-d6), δ: 5.83 (s, 2H), 6.75 (s, 2H), 6.88-7.54 (m, 8H), 7.93-8.05(m, 2H), 10.18 (s, 1H).