Compound 12: (4-(Ethoxycarbonyl)-1-phenyl-1H-pyrazol-5-olate)sodium

DOI: 10.14469/hpc/11257 Metadata

Created: 2022-10-03 09:19

Last modified: 2024-06-27 15:18

Author: Henry Rzepa

License: Creative Commons: Public Domain Dedication 1.0

Funding: (none given)

Description

1H and 13C primary NMR, IR and crystal data for (4-(Ethoxycarbonyl)-1-phenyl-1H-pyrazol-5-olate)sodium (12): NaOMe in MeOH (0.5 M; 1.71 mL, 0.853 mmol, 1.00 equiv) was added with stirring to pyrazolone 6 (198 mg, 0.853 mmol, 1.00 equiv) in MeOH (5.0 mL) at 65 °C. The mixture was heated at 65 °C for 18 h, after which the mixture was cooled to room temperature, the mixture was co-evaporated to dryness with Et2O (4 x 15 mL). The precipitate was suspended in Et2O, collected by filtration and dried in vacuo. Na-pyrazolone complex 12 (166 mg, 0.653 mmol, 77%) was obtained as a white solid, essentially pure by its 1H NMR spectrum. Crystals suitable for X-ray crystallography were obtained by slow evaporation from a MeOH solution of complex 12. 1H-NMR (400 MHz, CD3OD): δ (ppm) = 7.80 (d, J = 8.0 Hz, 2H), 7.65 (s, 1H), 7.37 (t, J = 7.8 Hz, 2H), 7.16 (t, J = 7.4 Hz, 1H), 4.21 (q, J = 7.1 Hz, 2H), 1.32 (t, J = 7.1 Hz, 3H). 13C{1H}-NMR (101 MHz, CD3OD): δ (ppm) = 167.5, 165.6, 142.6, 141.3, 129.5, 125.7, 122.5, 94.3, 59.6, 15.0. IR (Diamond-ATR, neat) νmax (cm-1) = 1653, 1598, 1560, 1522, 1499, 1454, 1411, 1381, 1352, 1321, 1221, 1191, 1103, 1075, 939, 785, 755, 691. HRMS (ES-ToF) m/z: [M + H]+ calc. for (C12H12N2O3Na)+: 255.0740, found: 255.0754. Major peak found at m/z: [M + H + CH3CN]+ calc. for (C14H15N3O3Na)+: 296.1006, found: 296.1021. m.p.: >300 °C (MeOH) (decomp.). Anal. Calcd for C12H11N2O3Na∙H2O: C, 52.94; H, 4.81; N, 10.29. Found: C, 53.90; H, 4.28; N, 10.14.

Member of collection / collaboration

DOIDescription
10.14469/hpc/10386 Syntheses and Characterization of Main Group, Transition Metal, Lanthanide and Actinide Complexes of Bidentate Acylpyrazolone Ligands

Members

DOIDescription
10.14469/hpc/11555 NMR Data for Compound 12.
10.14469/hpc/11554 IR Data for Compound 12.
10.14469/hpc/11328 Crystal data for (4-(Ethoxycarbonyl)-1-phenyl-1H-pyrazol-5-olate)sodium (12)

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