90
A. Katrusiak et al. / Journal of Molecular Structure 998 (2011) 84–90
143.7, 159.6, 173.6. MS(m/z, M+): 156.0 (100%). Anal. Calcd for
C6H8N2O3 (156.14): C, 46.15; H, 5.16; N, 17.94. Found C, 45.92;
H, 5.08; N, 17.34.
solution by evaporation. The diffraction data were recorded using
a 4-circle KUMA KM4-CCD diffractometer. The structures were
solved by direct methods with program Shelxs-97 and refined with
Shelxl-97 [19]. The crystal data of 2ÀÅH3O+ and 4A have been listed
in Table 2. The crystal structures have been also deposited with the
Cambridge Crystallographic Database Centre as supplementary
publications Nos. CCDC 771942 and CCDC 771943 copies can be
tabulated in Supplementary information, Tables S1–S12.
4.3. Methyl 1-methyl-6-oxopyridazine-3-carboxylate 5A and methyl
6-methoxypyridazine-3-carboxylate 5B
For 5A: Yield 37%; m.p. 189–191 °C; 1H NMR (CDCl3) d 3.36 (s,
3H), 3.85 (s, 3H), 6.97 (d, J = 9.9 Hz, 1H), 7.84 (d, J = 9.9 Hz, 1H);
13C NMR d 38.9, 52.6, 129.4, 132.1, 136.1, 160.6, 162.6. MS(m/z,
M+): 168.0 (7%). Anal. Calcd for C7H8N2O3 (168.15): C, 50.00; H,
4.80; N, 16.66. Found C, 49.95; H, 4.61; N, 16.34.
Appendix A. Supplementary material
For 5B: Yield 67%; m.p. 99–100 °C; 1H NMR (CDCl3) d 3.89 (s,
3H), 3.98 (s, 3H), 6.97 (d, J = 9.6 Hz, 1H), 7.86 (d, J = 9.6 Hz, 1H);
13C NMR d 40.5, 52.6, 128.4, 131.7, 135.3, 159.6, 162.3. MS(m/z,
M+): 168.0 (9%). Anal. Calcd for C7H8N2O3 (168.15): C, 50.00; H,
4.80; N, 16.66. Found C, 49.87; H, 4.72; N, 16.51.
Supplementary data associated with this article can be found, in
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4.4. 1-Methyl-6-oxopyridazine-3-carboxylic acid 6
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(a) To 1.56 g (10 mmol) of 3A in acetic acid 0.79 g (10 mmol) of
bromine was added dropwise. The reaction mixture was stir-
red for 2 h at 70 °C then poured into water, alkalized with
NH4OH and extracted with dichloromethane. The extracts
dried with MgSO4 and evaporated. Crude products were
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4.4.1. X-ray diffraction
The single crystals of compounds 2ÀÅH3O+ and 4A for X-ray dif-
fraction measurements were grown from the dichloromethane