9426
Y. Lu et al. / Tetrahedron 69 (2013) 9422e9427
conformer), 13C NMR (100 MHz, CDCl3):
d
170.0, 150.0, 146.8, 137.6,
138.5, 136.3, 129.8, 126.5, 122.9, 23.9, 19.2; GCeMS (EI, m/z): 194
[M]þ.
134.6, 134.3, 131.0, 129.6, 129.3, 128.1, 127.4, 125.7, 125.2, 125.1, 39.4,
36.8, 22.8, 22.2; GCeMS (EI, m/z): 194 [M]þ.
4.2.14. N-(2-Chloro-6-nitrophenyl)acetanilide (2p). White solid
(21 mg, 48% yield), mp: 190e191 ꢀC (lit44 190e191 ꢀC). The crude
product was purified by preparative HPLC on a C18 reversed-phase
4.2.7. N-(2-Nitrophenyl)maleimide (2g). White solid (18 mg, 40%
yield), mp: 130e131 ꢀC. Column chromatography (petroleum ether/
EtOAc¼2:1, Rf¼0.44). The NMR data are consistent with those re-
column (5
mm, 10*250 mm) using 65% (v/v) aqueous methanol
ported in the literature.37 1H NMR (400 MHz, CDCl3):
d 8.17 (d,
solution as eluent with the use of a UV detector at 254 nm. 1H NMR
J¼8.0 Hz, 1H, AreH), 7.77 (t, J¼8.0 Hz, 1H, AreH), 7.62 (t, J¼8.0 Hz,
(400 MHz, DMSO-d6):
d
10.27 (br s, 1H, NH), 7.91 (d, J¼8.0 Hz, 2H,
1H, AreH), 7.44 (d, J¼8.0 Hz, 1H, AreH), 6.94 (s, 2H, CH); 13C NMR
AreH), 7.50 (t, J¼8.0 Hz, 1H, AreH), 2.07 (s, 3H, COCH3); 13C NMR
(100 MHz, CDCl3):
d
168.6, 145.5, 135.1, 134.4, 131.0, 129.9, 126.0,
(100 MHz, DMSO-d6): d 168.6, 147.2, 134.1, 131.4, 128.2, 127.6, 123.6,
125.2; GCeMS (EI, m/z): 218 [M]þ.
22.6; GCeMS (EI, m/z): 214 [M]þ.
4.2.8. N-(4-Methyl-2-nitrophenyl)acetamide
(2i). Yellow
solid
4.2.15. N-(2-Methoxy-4-nitrophenyl)acetamide (2q). Yellow solid
(30 mg, 71% yield); mp: 136e138 ꢀC (lit45 139.5e140.5 ꢀC). Column
chromatography (petroleum ether/EtOAc¼1:1, Rf¼0.40). 1H NMR
(38 mg, 98% yield), mp: 95e96 ꢀC. Column chromatography (pe-
troleum ether/EtOAc¼4:1, Rf¼0.45). The NMR data are consistent
with those reported in the literature.38 1H NMR (400 MHz, CDCl3):
(400 MHz, CDCl3):
d
8.57 (d, J¼9.0 Hz,1H, AreH), 8.02 (br s,1H, NH),
d
10.22 (br s, 1H, NH), 8.63 (d, J¼8.6 Hz, 1H, AreH), 8.01 (s, 1H,
AreH), 7.46 (d, J¼8.6 Hz, 1H, AreH), 2.39 (s, 3H, CH3), 2.28 (s, 3H,
COCH3); 13C NMR (100 MHz, CDCl3):
169.1, 137.1, 136.4, 133.6,
132.6, 125.7, 122.3, 25.7, 20.7; GCeMS (EI, m/z): 194 [M]þ.
7.90 (dd, J¼9.0, 2.4 Hz, 1H, AreH), 7.74 (d, J¼2.4 Hz, 1H, AreH), 4.00
(s, 3H, OMe), 2.27 (s, 3H, COCH3); 13C NMR (100 MHz, CDCl3):
d
d 168.8, 147.3, 143.1, 134.0, 118.4, 117.9, 105.3, 56.5, 25.2; GCeMS (EI,
m/z): 210 [M]þ.
4.2.9. N-(4-Chloro-2-nitrophenyl)acetanilide
(2j). Yellow solid
4.2.16. N-(5-Methyl-2-nitrophenyl)acetamide (2r). Yellow solid
(24 mg, 61% yield), mp: 84e85 ꢀC. Column chromatography (pe-
troleum ether/EtOAc¼4:1, Rf¼0.55). 1H NMR (400 MHz, CDCl3):
(41 mg, 96% yield), mp: 99e100 ꢀC. Column chromatography (pe-
troleum ether/EtOAc¼4:1, Rf¼0.4). The NMR data are consistent
with those reported in the literature.39 1H NMR (400 MHz, CDCl3):
d
10.42 (br s, 1H, NH), 8.60 (s, 1H, AreH), 8.11 (d, J¼8.4 Hz, 1H,
d
10.26 (br s, 1H, NH), 8.78 (d, J¼9.2 Hz, 1H, AreH), 8.20 (s, 1H,
AreH), 6.97 (d, J¼8.4 Hz, 1H, AreH), 2.44 (s, 3H, CH3), 2.29 (s, 3H,
AreH), 7.61 (d, J¼9.2 Hz, 1H, AreH), 2.31 (s, 3H, COCH3); 13C NMR
COCH3); 13C NMR (100 MHz, CDCl3):
d 169.2, 148.2, 135.0, 134.3,
(100 MHz, CDCl3):
d
169.1, 136.5, 136.1, 133.7, 128.5, 125.4, 123.5,
125.9, 124.3, 122.2, 25.8, 22.3; GCeMS (EI, m/z): 194 [M]þ.
25.77; GCeMS (EI, m/z): 214 [M]þ.
4.2.17. N-(5-Bromo-2-nitrophenyl)acetamide (2s). Yellow solid
(34 mg, 66% yield), mp: 142e143 ꢀC (lit44 140 ꢀC). Column chro-
matography (petroleum ether/EtOAc¼4:1, Rf¼0.52). 1H NMR
4.2.10. N-(4-Bromo-2-nitrophenyl)acetamide (2k). Yellow solid
(47 mg, 91% yield), mp: 106e107 ꢀC. Column chromatography
(petroleum ether/EtOAc¼4:1, Rf¼0.33). The NMR data are consis-
tent with those reported in the literature.40 1H NMR (400 MHz,
(400 MHz, CDCl3):
d
10.41 (br s,1H, NH), 9.06 (d, J¼2.0 Hz,1H, AreH),
8.09 (d, J¼9.0 Hz, 1H, AreH), 7.31 (dd, J¼9.0, 2.0 Hz, 1H, AreH), 2.31
CDCl3):
d
10.27 (br s, 1H, NH), 8.72 (d, J¼9.2 Hz, 1H, AreH), 8.35 (s,
(s, 3H, COCH3); 13C NMR (100 MHz, CDCl3):
d 169.2, 135.8, 134.9,
1H, AreH), 7.74 (d, J¼9.2 Hz, 1H, AreH), 2.30 (s, 3H, COCH3); 13C
131.7, 127.0, 126.6, 124.8, 25.8; GCeMS (EI, m/z): 258 [M]þ.
NMR (100 MHz, CDCl3):
d 169.1, 138.9, 136.6, 134.1, 128.3, 123.7,
115.4, 25.8; GCeMS (EI, m/z): 258 [M]þ.
4.2.18. N-(2,4-Dichloro-6-nitrophenyl)acetamide (2t). White solid
(28 mg, 56% yield), mp: 180e181 ꢀC. Column chromatography
(petroleum ether/EtOAc¼4:1, Rf¼0.63). The NMR data are consis-
tent with those reported in the literature.46 1H NMR (400 MHz,
4.2.11. N-(4-Methoxy-2-nitrophenyl)acetamide (2l). Yellow solid
(36 mg, 86% yield), mp: 115e116 ꢀC. Column chromatography
(petroleum ether/EtOAc¼2:1, Rf¼0.37). The NMR data are consis-
tent with those reported in the literature.41 1H NMR (400 MHz,
CDCl3):
d
7.86 (d, J¼1.6 Hz, 1H, AreH), 7.73 (br s, 1H, NH), 7.70 (d,
J¼1.6 Hz, AreH), 2.24 (s, 1H, COCH3); 13C NMR (100 MHz, CDCl3):
CDCl3):
J¼3.0 Hz, 1H, AreH), 7.23 (dd, J¼9.2, 3.0 Hz, 1H, AreH), 3.86 (s, 3H,
OCH3), 2.27 (s, 3H, COCH3); 13C NMR (100 MHz, CDCl3):
168.9,
d
10.05 (br s, 1H, NH), 8.63 (d, J¼9.2 Hz, 1H, AreH), 7.66 (d,
d 168.2, 146.0, 134.1, 132.7, 132.2, 127.2, 124.2, 23.7; GCeMS (EI, m/
z): 248 [M]þ.
d
155.1, 137.2, 128.6, 124.0, 123.6, 108.6, 56.1, 25.6; GCeMS (EI, m/z):
4.2.19. N-(3,5-Dimethoxy-2-nitrophenyl)acetamide
(2u). Yellow
210 [M]þ.
solid (18 mg, 38% yield), mp: 148e149 ꢀC. Column chromatography
(petroleum ether/EtOAc¼2:1, Rf¼0.37). 1H NMR (400 MHz, CDCl3):
4.2.12. N-(4-Acetyl-2-nitrophenyl)acetamide (2m). Yellow solid
(33 mg, 74% yield), mp: 144e145 ꢀC (lit42 140e141 ꢀC). Column
chromatography (petroleum ether/EtOAc¼1:1, Rf¼0.59). 1H NMR
d
9.19 (br s, 1H, NH), 7.69 (d, J¼2.2 Hz, 1H, AreH), 6.28 (d, J¼2.2 Hz,
1H, Ar-H), 3.89 (s, 3H, OCH3), 3.87 (s, 3H, OCH), 2.22 (s, 3H, COCH3);
13C NMR (100 MHz, CDCl3):
d 169.0, 163.7, 155.6, 135.4 (over-
(400 MHz, CDCl3):
d
10.57 (br s, 1H, NH), 8.94 (d, J¼8.9 Hz, 1H,
lapping), 97.8, 95.8, 56.8, 56.1, 25.9; GCeMS (EI, m/z): 240 [M]þ.
AreH), 8.81 (d, J¼1.9 Hz, 1H, AreH), 8.22 (dd, J¼8.9, 1.9 Hz, 1H,
AreH), 2.65 (s, 3H, p-COCH3), 2.35 (s, 3H, COCH3); 13C NMR
4.2.20. N-(2-Nitronaphthalen-1-yl)acetamide (2v). Yellow solid
(14 mg, 30% yield), mp: 204e205 ꢀC (lit47 202e203 ꢀC). Column
chromatography (petroleum ether: EtOAc¼1:1, Rf¼0.46). 1H NMR
(100 MHz, CDCl3):
d 194.9, 169.3, 138.5, 135.7, 135.3, 131.8, 126.4,
122.0, 26.6, 26.0; GCeMS (EI, m/z): 222 [M]þ.
(400 MHz, DMSO-d6):
d 10.54 (br s, 1H, NH), 8.31e8.20 (m, 1H,
4.2.13. N-(2-Methyl-6-nitrophenyl)acetamide (2o). White solid
(28 mg, 72% yield), mp: 154e155 ꢀC. Column chromatography
(petroleum ether/EtOAc¼4:1, Rf¼0.38). The NMR data are consis-
tent with those reported in the literature.43 1H NMR (400 MHz,
AreH), 8.17e8.07 (m, 1H, AreH), 8.04 (d, J¼8.8 Hz, 1H, AreH), 7.95
(d, J¼8.8 Hz, 1H, AreH), 7.81e7.72 (m, 2H, AreH), 2.18 (s, 3H); 13C
NMR (100 MHz, DMSO-d6): d 169.0, 142.7, 134.8, 129.1, 128.8, 128.3,
127.9, 127.6, 127.1, 124.8, 120.5, 22.9; GCeMS (EI, m/z): 230 [M]þ.
CDCl3):
J¼8.0 Hz, 1H, AreH), 7.27 (t, J¼8.0 Hz, 1H, AreH), 2.32 (s, 3H,
COCH3), 2.22 (s, 3H, CH3); 13C NMR (100 MHz, CDCl3):
168.5, 145.1,
d
8.35 (br s, 1H, NH), 7.82 (d, J¼8.0 Hz, 1H, AreH), 7.51 (d,
4.2.21. o-Nitroaniline (2aa). Yellow solid (213 mg, 77% yield), mp:
69e70 ꢀC. Column chromatography (petroleum ether/EtOAc¼4:1,
d