Compound 13: (4-Benzoyl-1-(4-methoxybenzyl)-1H-pyrazol-5-olate)sodium
DOI: 10.14469/hpc/11712 Metadata
Created: 2022-11-05 15:04
Last modified: 2024-06-03 13:00
License: Creative Commons: Public Domain Dedication 1.0
Funding: (none given)
Description
(4-Benzoyl-1-(4-methoxybenzyl)-1H-pyrazol-5-olate)sodium (13): NaOMe (0.5 M in MeOH; 1.19 mL, 0.597 mmol, 1.00 equiv) was added with stirring to pyrazolone 10 (184 mg, 0.597 mmol, 1.00 equiv) in MeOH (3.5 mL) at 65 °C. The mixture was heated at reflux for 14 h, H2O (20 mL) was added, after which the mixture was cooled to room temperature. The precipitate was collected by filtration, washed with H2O (3 x 5.0 mL) and dried in vacuo. Na-pyrazolone complex 13 (113 mg, 0.342 mmol, 57%) 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 an EtOH solution of complex 13. 1H-NMR (400 MHz, CD3OD): δ (ppm) = 7.97 – 7.90 (m, 1H), 7.71 – 7.64 (m, 2H), 7.51 – 7.40 (m, 2H), 7.38 (s, 1H), 7.18 (d, J = 8.4 Hz, 2H), 6.83 (d, J = 8.6 Hz, 2H), 4.93 (s, 2H), 3.75 (s, 3H). 13C{1H}-NMR (101 MHz, CD3OD): δ (ppm) = 190.9, 165.9, 160.2, 143.0, 142.7, 131.9, 131.3, 129.7, 129.3, 129.0, 114.7, 105.0, 55.6, 48.0. IR (Diamond-ATR, neat) νmax (cm-1) = 1606, 1575, 1496, 1485, 1430, 1375, 1316, 1241, 1215, 1173, 1024, 891, 803, 743, 705. HRMS (ES-ToF) m/z: [M + H + CH3CN]+ calc. for (C20H19N3O3Na)+: 372.1319, found: 372.1332. m.p.: >90 °C (MeOH) (decomp.). Anal. Calcd for C18H15N2O3Na ∙ 1.2 H2O: C, 61.43; H, 4.98; N, 7.96. Found: C, 60.99; H, 4.58; N, 7.79.
Files
| Filename | Size | Type | Description |
|---|---|---|---|
| 13.cdxml | 8KB | chemical/x-cdxml | Chemdraw connection table |
| 13.cdxml | 8KB | chemical/x-cdxml | Chemdraw connection table V2 |
| 13.png | 31KB | image/png | Image representation |
| 13.mol | 2KB | chemical/x-mdl-molfile | MDL Molfile |
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 |
Subject Keywords
| Keyword | Value |
|---|---|
| inchi | InChI=1S/C18H16N2O3.Na/c1-23-15-9-7-13(8-10-15)12-20-18(22)16(11-19-20)17(21)14-5-3-2-4-6-14;/h2-11,22H,12H2,1H3;/q;+1/p-1 |
| inchikey | IBHYFRMZZCBYJC-UHFFFAOYSA-M |