Compound 11: (4-(Ethoxycarbonyl)-1-(4-methoxybenzyl)-1H-pyrazol-5-olate)sodium
DOI: 10.14469/hpc/11298 Metadata
Created: 2022-10-08 08:58
Last modified: 2024-06-27 17:46
License: Creative Commons: Public Domain Dedication 1.0
Funding: (none given)
Description
Crystal, IR and NMR data for (4-(Ethoxycarbonyl)-1-(4-methoxybenzyl)-1H-pyrazol-5-olate)sodium (11): NaOMe (0.5 M in MeOH; 1.62 mL,0.811 mmol, 1.00 equiv) was added with stirring to pyrazolone 8 (224 mg, 0.811 mmol, 1.00 equiv) in MeOH (60 mL) at 65 °C. After heating at reflux for 18 h, the mixture was cooled to room temperature and 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 11 (209 mg, 0.701 mmol, 86%) 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. 1H-NMR (400 MHz, CD3OD): δ (ppm) = 7.48 (s, 1H), 7.13 (d, J = 8.5 Hz, 2H), 6.86 – 6.77 (m, 2H), 4.91 (s, 2H), 4.18 (q, J = 7.1 Hz, 2H), 3.74 (s, 3H), 1.30 (t, J = 7.1 Hz, 3H). 13C{1H}-NMR (101 MHz, CD3OD): δ (ppm) = 167.6, 165.2, 160.2, 141.1, 132.2, 129.6, 114.7, 93.8, 59.5, 55.6, 48.1, 15.0. IR (Diamond-ATR, neat) νmax (cm-1) = 1663, 1653, 1647, 1559, 1508, 1411, 1320, 1243, 1211, 1171, 1094, 1030, 990, 786. HRMS (ES-ToF) m/z: [M + H + CH3CN]+ calc. for (C16H19N3O4Na)+: 340.1268, found: 340.1283. m.p.: 134 – 136 °C (MeOH). Anal. Calcd for C14H15N2NaO4∙H2O: C, 53.16; H, 5.42; N, 8.86. Found: C, 52.72; H, 5.03; N, 8.78.
Member of collection / collaboration
| DOI | Description |
|---|---|
| 10.14469/hpc/10386 | Syntheses and Characterization of Main Group, Transition Metal, Lanthanide and Actinide Complexes of Bidentate Acylpyrazolone Ligands |
Members
| DOI | Description |
|---|---|
| 10.14469/hpc/11562 | NMR Data for Compound 11. |
| 10.14469/hpc/11561 | IR data for Compound 11. |
| 10.14469/hpc/11327 | Crystal data for Compound 11 |