S.P. Shukla et al. / Tetrahedron 68 (2012) 9035e9044
9043
147.8, 139.5, 134.3, 131.8, 129.7, 129.2, 128.8, 125.5, 117.3, 105.5,
103.4, 61.2, 43.8, 34.2, 25.0, 13.9; HRMS calcd for C21H22NO3
J¼2.9 Hz, 1H, CHaromatic), 7.70 (d, J¼8.0 Hz, 1H, CHaromatic), 7.44e7.41
(m, 2H, CHaromatic), 7.24e7.18 (m, 4H, CHaromatic), 4.06 (q, J¼7.3 Hz,
([MþH]þ) 336.1600; found 336.1589. IR
n
(cmꢁ1) (liquid film): 2961,
2H, CH2CH3), 2.42 (s, 3H, PhCH3), 0.81 (t, J¼7.3 Hz, 3H, CH2CH3); 13
C
2924, 2855, 1716, 1633, 1615, 1558, 1511, 1463, 1337, 1374, 1262,
1099, 1019, 861, 844, 796, 750, 628.
NMR (100 MHz, CDCl3) d: 171.5, 160.9, 153.7, 149.9, 143.6, 140.1,
136.7, 131.9, 128.2, 128.1, 122.5, 120.6, 119.2, 106.5, 61.7, 20.6, 11.9;
HRMS calcd C19H17NO3 (Mþ) 307.1208; found 307.1205. IR (cmꢁ1
n
)
4.3.10. Ethyl 3-butyl-1-hydroxyacridine-2-carboxylate (4j). The
product was obtained as greenish yellow needle crystals in hexane/
CH2Cl2 (113.2 mg, 70%); mp 100e103 ꢀC; Rf (10% ethyl acetate/
(liquid film): 2925, 2852, 1733, 1630, 1615, 1515, 1445, 1372, 1266,
1243, 1101, 1020, 963, 831, 749.
hexane) 0.38; 1H NMR (400 MHz, CDCl3)
d: 13.33 (s, 1H, OH), 9.31 (s,
4.3.15. Ethyl 1-hydroxy-3-phenyl-2-naphthoate (4o). The product
was obtained as light yellow semi solid (102.3 mg, 70%); Rf (5% ethyl
1H, CHaromatic), 8.16 (d, J¼8.8 Hz, 1H, CHaromatic), 8.03 (d, J¼8.1 Hz,
1H, CHaromatic), 7.84e7.80 (m, 1H, CHaromatic), 7.53 (t, J¼7.3 Hz, 1H,
CHaromatic), 7.49 (s, 1H, CHaromatic), 4.52 (q, J¼7.3 Hz, 2H, CH2CH3),
3.12 (t, J¼7.3 Hz, 2H, CH2), 1.70e1.62 (m, 2H, CH2), 1.50e1.41 (m, 5H,
CH2þCH2CH3), 0.96 (t, J¼7.3 Hz, 3H, CH2CH3); 13C NMR (100 MHz,
acetate/hexane) 0.78; 1H NMR (400 MHz, CDCl3)
d: 12.27 (s, 1H,
OH), 8.17 (d, J¼8.8 Hz, 1H, CHaromatic), 8.00 (d, J¼8.8 Hz, 1H, CHar-
omatic), 7.78 (t, J¼8.0 Hz, 1H, CHaromatic), 7.50 (t, J¼7.3 Hz, 1H, CHar-
omatic), 7.36e7.29 (m, 5H, CHaromatic), 7.19 (s, 1H, CHaromatic), 3,98 (q,
J¼7.3 Hz, 2H, CH2CH3), 0.72 (t, J¼6.6 Hz, 3H, CH2CH3); 13C NMR
CDCl3) d: 172.4, 164.0, 150.8, 150.0, 144.3, 134.4, 131.8, 129.2, 128.9,
125.8, 125.5, 121.1, 118.5, 104.3, 61.9, 37.1, 33.7, 22.8, 14.10, 14.06;
(100 MHz, CDCl3) d: 171.8, 161.1, 140.6, 139.4, 136.1, 135.5, 129.7,
HRMS calcd for C20H22NO3 ([MþH]þ) 324.1600; found 324.1598. IR
128.3, 128.1, 127.3, 125.6, 123.94, 123.89, 121.2, 106.1, 61.0, 13.0;
n
(cmꢁ1) (liquid film): 2952, 2924, 2858, 1630, 1615, 1458, 1371,
HRMS calcd C19H16O3 (Mþ) 292.1099; found 292.1089. IR (cmꢁ1
n )
1338, 1264, 1107, 818, 744.
(liquid film): 2923, 2852, 1630, 1457, 1258, 1018, 751.
4.3.11. Ethyl 1-hydroxy-3-(phenoxymethyl)acridine-2-carboxylate
(4k). The product was obtained as green semi solid (128.8 mg,
69%); Rf (10% ethyl acetate/hexane) 0.25; 1H NMR (400 MHz, CDCl3)
4.3.16. Ethyl 1-hydroxy-3-p-tolyl-2-naphthoate (4p). The product
was obtained as white crystals in hexane/CH2Cl2 (113.3 mg, 74%);
mp 114e116 ꢀC; Rf (5% ethyl acetate/hexane) 0.72; 1H NMR
d
: 13.32 (s, 1H, OH), 9.37 (s, 1H, CHaromatic), 8.21 (d, J¼8.8 Hz, 1H,
(300 MHz, CDCl3)
d
: 12.21 (s, 1H, OH), 8.41 (d, J¼7.8 Hz, 1H, CHar-
CHaromatic), 8.07 (d, J¼8.8 Hz, 1H, CHaromatic), 7.96 (s, 1H, CHaromatic),
7.85 (t, J¼7.3 Hz, 1H, CHaromatic), 7.57 (t, J¼7.7 Hz, 1H, CHaromatic),
7.33e7.29 (m, 2H, CHaromatic), 7.03e6.96 (m, 3H, CHaromatic), 5.48 (s,
2H, CH2OPh), 4.04 (q, J¼7.3 Hz, 2H, CH2CH3), 1.36 (t, J¼7.3 Hz, 3H,
omatic), 7.72 (d, J¼7.2 Hz, 1H, CHaromatic), 7.60e7.58 (m, 1H, CHar-
omatic), 7.54e7.49 (m, 2H, CHaromatic), 7.36e7.19 (m, 4H, CHaromatic),
4.04 (q, J¼6.9 Hz, 2H, CH2CH3), 2.41 (s, 3H, PhCH3), 0.79 (t, J¼7.2 Hz,
3H, CH2CH3); 13C NMR (75 MHz, CDCl3)
d: 171.8, 161.1, 140.6, 139.4,
CH2CH3); 13C NMR (100 MHz, CDCl3)
d
: 171.8, 169.7, 164.2, 158.7,
136.1, 135.5, 131.8, 129.6, 128.8, 128.1, 127.3, 125.6, 123.9, 121.1, 106.1,
143.2, 140.0, 137.8, 135.4, 134.6, 132.2, 129.5, 129.1, 126.1, 120.9,
119.5, 119.0, 114.7, 102.8, 68.2, 61.0, 14.1; HRMS calcd for C23H19NO4
61.0, 21.1, 13.0; HRMS calcd C20H18O3 (Mþ) 306.1256; found
306.1251. IR
n
(cmꢁ1) (liquid film): 2924, 2854, 1731, 1660, 1651,
(Mþ) 373.1314; found 373.1314. IR
n
(cmꢁ1) (KBr): 2984, 2931, 1655,
1608, 1514, 1373, 1305, 1261, 1108, 1020, 831, 805, 733. Crystallo-
graphic data for 4p have been deposited with the Cambridge
Crystallographic Data Centre. CCDC 847471, contain all crystallo-
graphic details of this publication and is available free of charge at
the following address: Cambridge Crystallographic Data Centre, 12
Union Road, GB-Cambridge CB21EZ; fax: (þ44)1223-336-033; or
1631, 1617, 1229, 1509, 1371, 1327, 1280, 1161, 1116, 849, 754, 637.
4.3.12. Ethyl 5-hydroxy-7-p-tolylquinoline-6-carboxylate (4l). The
product was obtained as brown needle crystals in hexane/CH2Cl2
(121.4 mg, 79%); mp 107e110 ꢀC; Rf (10% ethyl acetate/hexane)
0.25; 1H NMR (400 MHz, CDCl3)
d: 12.19 (s, 1H, OH), 8.98 (dd, J¼1.5,
4.4 Hz, 1H, CHaromatic), 8.72e8.70 (m, 1H, CHaromatic), 7.48 (s, 1H,
CHaromatic), 7.44e7.40 (m, 1H, CHaromatic), 7.23e7.18 (m, 4H, CHar-
omatic), 4.03 (q, J¼7.3 Hz, 2H, CH2CH3), 2.36 (s. 3H, PhCH3), 0.81 (t,
4.3.17. Ethyl 1-hydroxy-3-(4-methoxyphenyl)-2-naphthoate (4q).
The product was obtained as white crystals in hexane/CH2Cl2
(127.3 mg, 79%); mp 127e129 ꢀC; Rf (5% ethyl acetate/hexane) 0.52;
J¼7.3 Hz, 3H, CH2CH3); 13C NMR (100 MHz, CDCl3)
d: 171.4, 160.8,
153.5, 149.9, 143.3, 139.8, 136.5, 132.4, 128.26, 128.16, 122.5, 120.6,
119.2, 106.8, 61.3, 21.2, 13.0; HRMS calcd for C19H17NO3 (Mþ)
1H NMR (300 MHz, CDCl3)
d: 12.16 (s, 1H, OH), 8.33 (d, J¼8.1 Hz, 1H,
307.1208; found 307.1208. IR
1515, 1374, 1321, 1258, 1155, 1094, 1020, 799, 614.
n
(cmꢁ1) (liquid film): 2926, 1645,
CHaromatic), 7.64 (d, J¼7.8 Hz, 1H, CHaromatic), 7.53 (t, J¼6.9 Hz, 2H,
CHaromatic), 7.46e7.41 (m, 1H, CHaromatic), 7.18e7.14 (m, 2H, CHar-
omatic), 6.84 (d, J¼8.4 Hz, 2H, CHaromatic), 3.98 (q, J¼7.2 Hz, 2H,
CH2CH3), 3.79 (s, 3H, PhOCH3), 0.77 (t, J¼7.2 Hz, 3H, CH2CH3); 13C
4.3.13. Ethyl 7-(3,5-dimethoxyphenyl)-5-hydroxy quinoline-6-
carboxylate (4m). The product was obtained as light yellow crys-
tals in hexane/CH2Cl2 (127.2 mg, 72%); mp 260e265 ꢀC; Rf (10%
NMR (75 MHz, CDCl3) d: 170.8, 160.2, 157.5, 137.9, 135.1, 134.4, 128.6,
128.4, 126.2, 124.6, 122.8, 120.2, 111.9, 105.1, 60.0, 54.4, 12.2; HRMS
ethyl acetate/hexane) 0.10; 1H NMR (400 MHz, CDCl3)
d: 12.16 (s,
calcd C20H18O4 (Mþ) 322.1205; found 322.1205. IR (cmꢁ1) (liquid
n
1H, OH), 8.92 (dd, J¼1.4, 2.2 Hz, 1H, CHaromatic), 8.65 (dd, J¼1.4,
8.8 Hz, 1H, CHaromatic), 7.44 (s, 1H, CHaromatic), 7.39e7.35 (m, 1H,
CHaromatic), 6.43e6.37 (m, 3H, CHaromatic), 4.04 (q, J¼7.3 Hz, 2H,
CH2CH3), 3.74 (s, 6H, PhOCH3), 1.18 (t, J¼7.3 Hz, 3H, CH2CH3); 13C
film): 2924, 2851, 1629, 1401, 1326, 1280, 1242, 1179, 1111, 1016,
822, 772.
4.3.18. Ethyl 1-hydroxy-3-(thiophen-3-yl)-2-naphthoate (4r). The
product was obtained as yellow crystals in hexane/CH2Cl2
(119.3 mg, 80%); mp 90e94 ꢀC; Rf (5% ethyl acetate/hexane) 0.76; 1H
NMR (100 MHz, CDCl3) d: 171.2, 160.8, 160.1, 153.5, 149.8, 144.6,
143.1, 138.5, 132.5, 122.1, 120.8, 119.4, 106.7, 99.2, 61.3, 60.4, 55.4,
14.1; HRMS calcd for C20H19NO5 (Mþ) 353.1263; found 353.1268. IR
NMR (400 MHz, CDCl3)
d
: 12.25 (s, 1H, OH), 8.34 (d, J¼8.1 Hz, 1H,
n
(cmꢁ1) (liquid film): 2922, 2852, 1636, 1401, 1326, 1280, 1242,
CHaromatic), 7.64 (d, J¼8.1 Hz, 1H, CHaromatic), 7.55e7.51 (m, 1H,
CHaromatic), 7.46e7.42 (m, 1H, CHaromatic), 7.21e7.19 (m, 1H, CHar-
omatic), 7.17 (s, 1H, CHaromatic), 7.11e7.09 (m, 1H, CHaromatic), 6.96 (d,
J¼5.9 Hz, 1H, CHaromatic), 4.04 (q, J¼7.3 Hz, 2H, CH2CH3), 0.89 (t,
1179, 1111, 1016, 832, 722.
4.3.14. Ethyl 5-hydroxy-7-p-tolylisoquinoline-6-carboxylate (4n).
The product was obtained as yellow needle crystals in hexane/
CH2Cl2 (112.2 mg, 73%); 110e112 mp ꢀC; Rf (10% ethyl acetate/
J¼7.3 Hz, 3H, CH2CH3); 13C NMR (100 MHz, CDCl3)
d: 171.7, 161.3,
143.6, 135.5, 133.9, 129.7, 129.3, 127.2, 125.8, 124.2, 123.93, 123.81,
hexane) 0.28; 1H NMR (400 MHz, CDCl3)
d: 12.22 (s,1H, OH), 7.97 (d,
121.4, 120.9, 106.0, 61.1, 13.1; HRMS calcd C17H14O3S ([M ꢁ H]þ)