Med Chem Res (2014) 23:2161–2168
2163
and the reaction mixture was stirred at 80 °C for 2–24 h,
until the reaction was over which was confirmed using
TLC. The reaction mixture was poured into six times its
volume of water, and then diluted hydrochloric acid was
added until the pH value is between three and four stirred
for a further 10 min. The crude final product was filtered
with suction, washed several times with cold water, and
then infrared dried. The product was crystallized from
methanol (Modi et al., 2011). The yield, melting point, and
spectral data of each compound are given below.
2.45(3H, s, –CH3). 13C NMR (CDCl3, 75 MHz): 212.
22(C=O), 182.49(C=O), 164.77(C=O), 158.59(Ar–C), 150.
87(Ar–C), 140.58(Ar–C), 138.27(Ar–C), 136.68(Ar–C),
128.81(Ar–C), 126.27(Ar–C), 124.32(Ar–C), 120.45(Ar–
C), 116.38(Ar–C), 108.97(Ar–C), 99.79(Ar–C), 44.
84(CH2–C), 18.35(CH3–C). Anal. Calcd. for C17H14N2O3:
C, 69.38; H, 4.79; O, 16.31. Found: C, 69.23; H, 4.82; O,
16.24. MS m/z: 295 (M?1).
2-(5-Fluoro-2,3-dioxoindolin-1-yl)-N-phenylacetamide
1
(4e) IR (KBr) cm-1: 3495, 1731, 1648, 1251. H NMR
2-(2,3-Dioxoindolin-1-yl)-N-phenylacetamide (4a) IR (KBr)
cm-1: 3490, 1731, 1649, 1253. 1HNMR(CDCl3, 300 MHz): d
9.90 (1H, s, –NH), 7.26–7.56 (5H, m, –C6H5), 6.93–7.64 (4H,
m, –C6H4), 4.57 (2H, s, –CH2). 13C NMR (CDCl3, 75 MHz):
211.12(C=O), 181.55(C=O), 164.33(C=O), 158.78(Ar–C),
150.87(Ar–C), 140.69(Ar–C), 138.16(Ar–C), 137.49(Ar–C),
128.81(Ar–C), 126.64(Ar–C), 124.34(Ar–C), 120.27(Ar–C),
117.34(Ar–C), 109.25(Ar–C), 98.72(Ar–C), 45.44(CH2–C).
Anal. Calcd. for C16H12N2O3: C, 68.56; H, 4.32; O, 17.13.
Found: C, 68.46; H, 4.24; O, 17.04. MS m/z: 281 (M?1).
(CDCl3, 300 MHz): d 9.98 (1H, s, –NH), 7.23–7.48 (5H,
m, –C6H5), 6.94–7.70 (3H, m, –C6H3), 4.51 (2H, s, –CH2).
13C NMR (CDCl3, 75 MHz): 211.39(C=O), 182.17(C=O),
164.60(C=O), 158.79(Ar–C), 152.34(Ar–C), 142.54(Ar–
C), 138.89(Ar–C), 138.11(Ar–C), 132.06(Ar–C), 128.
80(Ar–C), 127.57(Ar–C), 124.52(Ar–C), 120.28(Ar–C),
118.24(Ar–C), 102.26(Ar–C), 43.55(CH2–C). Anal. Calcd.
for C16H11FN2O3: C, 64.43; H, 3.72; O, 16.09. Found: C,
64.35; H, 3.60; O, 15.83. MS m/z: 299 (M?1).
2-(6-Fluoro-2,3-dioxoindolin-1-yl)-N-phenylacetamide
1
2-(5-Methyl-2,3-dioxoindolin-1-yl)-N-phenylacetamide
1
(4f) IR (KBr) cm-1: 3490, 1732, 1649, 1251. H NMR
(4b) IR (KBr) cm-1: 3501, 1733, 1649, 1251. H NMR
(CDCl3, 300 MHz): d10.04 (1H, s, –NH), 7.24–7.61 (5H,
m, –C6H5), 6.98–7.70 (3H, m, –C6H3), 4.52 (2H, s, –CH2).
13C NMR (CDCl3, 75 MHz): 212.09(C=O), 181.04(C=O),
164.50(C=O), 158.85(Ar–C), 152.16(Ar–C), 142.69(Ar–
C), 138.78(Ar–C), 138.19(Ar–C), 131.98(Ar–C), 128.
83(Ar–C), 127.70(Ar–C), 124.27(Ar–C), 120.11(Ar–C),
118.24(Ar–C), 102.20(Ar–C), 43.64(CH2–C). Anal. Calcd.
for C16H11FN2O3: C, 64.43; H, 3.72; O, 16.09. Found: C,
64.38; H, 3.65; O, 15.86. MS m/z: 299 (M?1).
(CDCl3, 300 MHz): d 9.90 (1H, s, –NH), 7.23–7.48 (5H,
m, –C6H5), 6.78–7.60 (3H, m, –C6H3), 4.47 (2H, s, –CH2),
2.27(3H, s, –CH3). 13C NMR (CDCl3, 75 MHz): 219.
87(C=O), 183.30(C=O), 164.77(C=O), 158.78(Ar–C), 148.
51(Ar–C), 138.83(Ar–C), 138.10(Ar–C), 133.62(Ar–C),
128.75(Ar–C), 125.24(Ar–C), 124.28(Ar–C), 120.32(Ar–
C), 117.78(Ar–C), 115.51(Ar–C), 103.56(Ar–C), 48.
00(CH2–C), 20.71(CH3–C). Anal. Calcd. for C16H12N2O3:
C, 69.38; H, 4.79; O, 16.31. Found: C, 69.43; H, 4.69; O,
16.20. MS m/z: 295 (M?1).
2-(5-Chloro-2,3-dioxoindolin-1-yl)-N-phenylacetamide
1
(4g) IR (KBr) cm-1: 3500, 1731, 1650, 1253. H NMR
2-(6-Methyl-2,3-dioxoindolin-1-yl)-N-phenylacetamide
(4c) IR (KBr) cm-1: 3491, 1731, 1649, 1251. H NMR
(CDCl3, 300 MHz): d 9.97(1H, s, –NH), 7.23–7.52 (5H, m,
1
–C6H5), 6.93–7.67 (3H, m, –C6H3), 4.51 (2H, s, –CH2). 13
C
(CDCl3, 300 MHz): d 9.84 (1H, s, –NH), 7.22–7.45 (5H,
m, –C6H5), 6.85–7.48 (3H, m, –C6H3), 4.47 (2H, s, –CH2),
2.50(3H, s, –CH3). 13C NMR (CDCl3, 75 MHz): 212.
32(C=O), 183.45(C=O), 164.73(C=O), 158.58(Ar–C), 151.
27(Ar–C), 140.73(Ar–C), 138.00(Ar–C), 137.60(Ar–C),
128.73(Ar–C), 126.23(Ar–C), 124.31(Ar–C), 120.33(Ar–
C), 116.50(Ar–C), 107.85(Ar–C), 95.71(Ar–C), 45.
94(CH2–C), 18.04(CH3–C). Anal. Calcd. for C16H12N2O3:
C, 69.38; H, 4.79; O, 16.31. Found: C, 69.27; H, 4.59; O,
16.25. MS m/z: 295 (M?1).
NMR (CDCl3, 75 MHz): 211.45(C=O), 182.12(C=O), 164.
49(C=O), 158.20(Ar–C), 149.08(Ar–C), 140.37(Ar–C),
138.07(Ar–C), 137.64(Ar–C), 129.21(Ar–C), 128.80(Ar–
C), 127.21(Ar–C), 124.64(Ar–C), 124.35(Ar–C), 120.
20(Ar–C), 112.40(Ar–C), 43.55(CH2–C). Anal. Calcd. for
C16H11ClN2O3: C, 61.06; H, 3.52; O, 15.25. Found: C, 60.
80; H, 3.41; O, 15.09. MS m/z: 315 (M?1).
2-(6-Chloro-2,3-dioxoindolin-1-yl)-N-phenylacetamide
1
(4h) IR (KBr) cm-1: 3491, 1731, 1648, 1253. H NMR
(CDCl3, 300 MHz): d 10.01 (1H, s, –NH), 7.24–7.53 (5H,
m, –C6H5), 6.92–7.87 (3H, m, –C6H3), 4.53 (2H, s, –CH2).
13C NMR (CDCl3, 75 MHz): 213.64(C=O), 180.10(C=O),
164.58(C=O), 158.66(Ar–C), 152.05(Ar–C), 143.99(Ar–
C), 138.88(Ar–C), 138.25(Ar–C), 132.46(Ar–C), 128.
2-(7-Methyl-2,3-dioxoindolin-1-yl)-N-phenylacetamide
1
(4d) IR (KBr) cm-1: 3507, 1732, 1651, 1252. H NMR
(CDCl3, 300 MHz): d 9.99 (1H, s, –NH), 7.28–7.55 (5H,
m, –C6H5), 7.02–7.64 (3H, m, –C6H3), 4.78 (2H, s, –CH2),
123