Molecules 2010, 15
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temperature for about 2 h under nitrogen. The precipitate was collected by filtration, washed with
MeOH (8 mL), H2O (8 mL) and MeOH (5 mL), respectively, and then dried under vacuum at room
temperature to obtain the corresponding 2-chloromethylquinazolinone derivatives 3a-3l. The following
title compounds were prepared as described above:
2-Chloromethylquinazolin-4(3H)-one (3a). Prepared from o-anthranilic acid (2a) as a white solid; m.p.
249-250 °C; 1H-NMR (DMSO-d6): δ 12.59 (br s, 1H), 8.12 (dd, J = 1.2, 7.2 Hz, 1H), 7.84 (dd, J = 1.2,
7.2 Hz, 1H), 7.68 (d, J = 8.0 Hz, 1H), 7.56 (t, J = 8.0 Hz, 1H), 4.55 (s, 2H); 13C-NMR (DMSO-d6): δ
161.79, 152.62, 148.47, 134.88, 127.52, 126.14, 121.52, 106.89, 43.53; ESI-MS: m/z 195.03 (M+H+).
2-Chloromethyl-7-chloroquinazolin-4(3H)-one (3b). Prepared from 7-chloro-2-aminobenzoic acid (2b)
1
as a white solid; m.p. 232-234 °C; H-NMR (DMSO-d6): δ 12.72 (br s, 1H), 8.10 (d, J = 8 Hz, 1H),
13
7.75 (s, 1H), 7.58 (d, J = 8 Hz, 1H), 4.55 (s, 2H); C-NMR (DMSO-d6): δ 161.15, 154.13, 149.53,
139.44, 128.10, 127.68, 126.64, 120.30, 43.29; ESI-MS: m/z 227.05 (M-H+).
2-Chloromethyl-5-chloroquinazolin-4(3H)-one (3c). Prepared from 6-chloro-2-aminobenzoic acid (2c)
1
as a white solid; m.p. 220-221 °C; H-NMR (DMSO-d6): δ 12.63 (br s, 1H), 7.74 (t, J = 8.0 Hz, 1H),
13
7.60 (d, J = 8.0 Hz, 1H), 7.54 (d, J = 8.0 Hz, 1H), 4.51 (s, 2H); C-NMR (DMSO-d6): δ 159.87,
153.35, 150.91, 134.56, 132.78, 129.76, 127.00, 118.42, 42.97; ESI-MS: m/z 227.08 (M-H+).
2-Chloromethyl-6-bromoquinazolin-4(3H)-one (3d). Prepared from 5-bromo-2-aminobenzoic acid (2d)
as a white solid; m.p. 240-242 °C; 1H-NMR (DMSO-d6): δ 12.80 (br s, 1H), 8.19 (d, J = 2.0 Hz, 1H),
7.98 (dd, J = 2.4, 8.0 Hz, 1H), 7.63 (d, J = 8.0 Hz, 1H), 4.55 (s, 2H); 13C-NMR (DMSO-d6): δ 160.62,
153.21, 147.37, 137.63, 129.80, 128.23, 123.07, 119.97, 43.34; ESI-MS: m/z 271.01 (M-H+).
2-Chloromethyl-7-bromoquinazolin-4(3H)-one (3e). Prepared from 4-bromo-2-aminobenzoic acid (2e)
as a white solid; m.p. 238-240 °C; 1H-NMR (DMSO-d6): δ 12.77 (br s, 1H), 8.02 (d, J = 8.0 Hz, 1H),
13
7.91 (s, 1H), 7.72 (d, J = 8.0 Hz, 1H), 4.55 (s, 2H); C-NMR (DMSO-d6): δ 161.24, 154.01, 149.56,
130.42, 129.67, 128.38, 128.10, 120.55, 43.28; ESI-MS: m/z 270.99 (M-H+).
2-Chloromethyl-6-fluoroquinazolin-4(3H)-one (3f). Prepared from 5-fluoro-2-aminobenzoic acid (2f)
as a white solid; m.p. 239-241 °C; 1H-NMR (DMSO-d6): δ 12.75 (br s, 1H), 7.76 (m, J = 8.0 Hz, 3H),
4.56 (s, 2H); 13C-NMR (DMSO-d6): δ 161.81, 161.17, 159.36, 152.06, 145.27, 130.35, 123.36, 123.00,
122.80, 110.91, 43.40; ESI-MS: m/z 211.06 (M-H+).
2-Chloromethyl-7-fluoroquinazolin-4(3H)-one (3g). Prepared from 7-fluoro-2-aminobenzoic acid (2g)
as a white solid; m.p. 247-249 °C; 1H-NMR (DMSO-d6): δ 12.72 (br s, 1H), 8.18 (dd, J = 2.4, 8.0 Hz,
1H), 7.48 (dd, J = 2.0, 8.0 Hz, 1H), 7.42 (dd, J = 2.4, 8.0 Hz, 1H), 4.55 (s, 2H); 13C-NMR (DMSO-d6):
δ 167.19, 164.70, 161.04, 154.07, 150.58, 129.15, 118.45, 115.83, 112.57, 43.25; ESI-MS: m/z 213.03
(M+H+).