J Fluoresc (2010) 20:1129–1137
1135
3-(5-(4-Nitrophenyl)-4,5-dihydro-1-phenyl-1H-pyrazol-3-
yl)-4-hydroxy-1-methyl quinolin-2(1H)-one(3j) Yield:
1.70 g (40%), mp. 212–213°C. IR (KBr): 3,460, 3,182,
1,660, 1,588, 1,510, 1,415 cm−1; 1H NMR (CDCl3) δ=3.40
(s, 3H, NCH3), 3.70(q, 1H, J=6.2 Hz, CH), 4.12(q, J=
6.3 Hz, 1H, CH), 5.02(t, J=6.3 Hz, 1H, CH), 6.80–7.10(m,
4H, ArH), 7.25–7.45(m, 5H, ArH), 7.60(d, 2H, J=8.2 Hz,
ArH), 8.22(d, 2H, J=8.2 Hz, ArH), 9.10(bs, 1H, OH). Anal.
Calcd. for C25H20N4O4 (440.15): C, 68.17; H, 4.58; N,
12.72. Found: C, 68.40; H, 4.32; N, 12.90%.
prism); IR (KBr): 3,558, 3,180, 1,680, 1,615, 1,540 cm−1;
1H NMR (CDCl3) δ=1.74(t, J=6.71 Hz, 2H, CH2), 3.45(s,
3H, NCH3), 3.50–3.58(s, 6H, 2 × OCH3), 3.86(t, J=
6.74 Hz, 2H, CH2), 4.0(q, J=7.6 & 6.5 Hz, 1H, CH),
4.32(q, J=7.6 Hz & 6.5 Hz, 1H, CHpyrazole), 4.81(t, J=7.8
& 6.5 Hz, 1H, CHpyrazole), 6.98–7.22(m, 4H, ArH), 7.62(d,
2H, J=7.8 Hz, ArH), 8.12(d, 2H, J=7.8 Hz, ArH). MS
(70e/v): m/z=424.00 [M+1, 100%], 395(50%), 383(80%),
361(55%), 345(50%), 317(60%), 272(40%), 178(72%), 128
(98%). Anal. Calcd. for C23H25N3O5 (423.47): C, 65.24; H,
5.95; N, 9.92. Found: C, 65.30; H, 5.82; N, 10.05%.
3-(5-(4-Chlorophenyl)-4,5-dihydro-1-(2-hydroxyethyl)-1H-
pyrazol-3-yl)-4-hydroxy -1-methylquinolin-2(1H)-one (3k)
Yield 2.15 g (60%); mp. 190–192°C (ethanol, yellow
prism); IR (KBr): 3,522, 3,125, 1,674, 1,610, and
3-(5-(4-Nitrophenyl)-4,5-dihydro-1-(2-hydroxyethyl)-1H-
pyrazol-3-yl)-4-hydroxy-1-methylquinolin-2(1H)-one (3o)
Yield 2.01 g (52%); mp. 194–195°C (ethanol, yellow
prism); IR (KBr): 3,512, 3,180, 1,671, 1,608, and
1
1,501 cm−1; H NMR (CDCl3) δ=1.81(t, J=7.1 Hz, 2H,
1
CH2), 3.5(s, 3H, NCH3), 3.86(t, J=6.7 Hz, 2H, CH2), 4.01
(dd, J=7.6 & 6.5 Hz, 1H, CH), 4.32(dd, J=7.6 Hz &
6.5 Hz, 1H, CH pyrazole), 4.80(dd, J=7.8 & 6.5 Hz, 1H,
CH pyrazole), 6.98–7.22(m, 4H, ArH), 7.62(d, 2H, J=7.8 Hz,
ArH). 8.12(d, 2H, J=7.8 Hz, ArH). Anal. Calcd. for
C21H20ClN3O3(397.86): C, 63.40; H, 5.07; N, 10.56.
Found: C, 63.50; H, 5.10; N, 10.70%.
1,512 cm−1; H NMR (CDCl3) δ=1.78(t, J=7.1 Hz, 2H,
CH2), 3.54(s, 3H, NCH3), 3.91(t, J=6.7 Hz, 2H, CH2), 4.12
(dd, J=7.6 & 6.5 Hz, 1H, CH), 4.38(dd, J=7.6 Hz &
6.5 Hz, 1H, CH pyrazole), 4.60(dd, J=7.8 & 6.5 Hz, 1H,
CH pyrazole), 6.90–7.15(m, 4H, ArH), 7.55(d, 2H, J=7.8 Hz,
ArH). 8.16(d, 2H, J=7.8 Hz, ArH). Anal. Calcd. for
C21H20N4O5(408.14): C, 61.76; H, 4.94; N, 13.72. Found:
C, 61.50; H, 5.11; N, 13.70%.
3-(5-(4-Bromophenyl)-4,5-dihydro-1-(2-hydroxyethyl)-1H-
pyrazol-3-yl)-4-hydroxy-1-methylquinolin-2(1H)-one (3l)
Yield: 2.40 g (64%), mp. 186–188°C (ethanol, yellow
prism); IR (KBr): 3,512, 3,195, 1,678, 1,605, 1,530 cm−1;
1H NMR (CDCl3) δ=1.77(t, J=6.4 Hz, 2H, CH2), 3.45(s,
3H, NCH3), 3.66(t, J=6.4 Hz, 2H, CH2), 3.92(dd, J=7.6 &
6.5 Hz, 1H, CH), 4.22(dd, J=7.6 Hz & 6.5 Hz, 1H,
CHpyrazole), 4.62(dd, J=7.8 & 6.5 Hz, 1H, CHpyrazole), 7.02–
7.30(m, 4H, ArH), 7.55(d, 2H, J=7.8 Hz, ArH). 8.44(d, 2H,
J=7.8 Hz, ArH). Anal. Calcd. for C21H20BrN3O3 (442.32):
C, 57.03; H, 4.56; N, 9.50. Found: C, 57.16; H, 4.72; N,
9.62%.
General Procedure for the isoxazol-3-yl)-4-hydroxy-1-
methylquinolin-2(1H)-one-(5a–e) To a mixture of chalcone
1 (0.01 mol), hydroxylamine hydrochloride 4 (0.69 g,
0.01 mol), sodium acetate (0.73 g, 0.01mole) and catalytic
amount of acetic acid (1 mL) in ethanol (15 mL) were
refluxed for 8–10 h (TLC Check, toluene: acetone 8:2). The
reaction mixture was cooled, concentrated and neutralized
with NaOH. The product was isolated and crystallized from
ethanol to afford 5 50–65% yields.
3-(5-(4-Chlorophenyl)-isoxazol-3-yl)-4-hydroxy-1-
methylquinolin-2(1H)-one-(5a) Yield 1.85 g (60%). mp.
225–226°C (ethanol, colorless flakes); IR (KBr): 3,431,
3,112, 1,685, 1,612, 1,515 cm−1; 1H NMR (CDCl3) δ=3.64
(s, 3H, NCH3), 7.32–7.50(m, 4H, ArH), 7.63(s, 1H, ArH),
7.96(d, 2H, J=8.1 Hz, ArH), 8.15(d, 2H, J=8.1ArH), 11.46
(bs, 1H, OH). MS (70 eV): m/z=353(M+1, 90%), 335
(10%), 309(10%), 280(10%), 241(20%), 228(15%), 215
(95%), 176(100%), 151(90%), 131(90%), 116(50%), 77
(98%), 63(60%), 51(40%). Anal. Calcd for C19H13ClN2O3
(352.5): C, 64.69; H, 3.71; N, 7.94. Found: C, 64.80; H,
3.85; N, 7.80%.
3-(5-(4-Methoxyphenyl)-4,5-dihydro-1-(2-hydroxyethyl)-
1H-pyrazol-3-yl)-4-hydroxy-1-methylquinolin-2(1H)-one
(3m) Yield 2.02 g (55%), mp. 202–204°C (ethanol, yellow
prism); IR (KBr): 3,502, 3,108, 1,675, 1,606, 1,515 cm−1;
1H NMR (CDCl3) δ=1.80(t, J=6.4 Hz, 2H, CH2), 3.40(s,
3H, NCH3), 3.52(s, 3H, OCH3), 3.60(t, J=6.4 Hz, 2H,
CH2), 3.97(q, J=7.6 & 6.5 Hz, 1H, CH), 4.30(q, J=7.6
Hz & 6.5 Hz, 1H, CH pyrazole), 4.75(t, J=7.8 & 6.5 Hz, 1H,
CH pyrazole), 6.90–7.20(m, 4H, ArH), 7.55(d, 2H, J=7.8 Hz,
ArH). 8.01(d, 2H, J=7.8 Hz, ArH). Anal. Calcd. for
C22H23N3O4 (393.45): C, 67.16; H, 5.89; N, 10.68. Found:
C, 67.22; H, 6.05; N, 10.72%.
3-[5-(4-Bromophenyl)-isoxazol-3-yl]-4-hydroxy-1-
methylquinolin-2-(1H)-one(5b) Yield: 1.90 g (65%), mp.
196–197°C (ethanol, colorless flakes); IR (KBr): 3,512,
3,234, 1,674, 1,611, 1,524 cm−1; 1H NMR (CDCl3) δ=3.72
(s, 3H, NCH3), 7.15–7.40(m, 4H, ArH), 7.66(s, 1H, ArH),
3-(5-(4-Dimethoxyphenyl)-4,5-dihydro-1-(2-hydroxyethyl)-
1H-pyrazol-3-yl)-4-hydroxy-1-methylquinolin-2(1H)-one
(3n) Yield 2.12 g (65%). mp. 221–223°C (ethanol, yellow