Sodium Hydroxide → 1-(4-Fluoro-benzyl)-2-oxo-1,2-dihydro-pyridine-3-carboxylic acid
Reaktionsgleichung
[F:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][N:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([O:15]C)=[O:14])[C:8]2=[O:17])=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([OH:15])=[O:14])[C:8]2=[O:17])=[CH:18][CH:19]=1Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
A solution of methyl 1-(4-fluorobenzyl)-2-oxo-1,2-dihydropyridine-3-carboxylate (2.4 g, 9.2 mmol, 1.0 eq) in MeOH (25 ml) was treated with 5 N aqueous sodium hydroxide (4.6 mL, 24 mmol, 2.6 eq) at room temperature and the reaction mixture was stirred for 15 h. The reaction mixture was concentrated in vacuo, diluted with water and the solution was extracted with ethyl acetate (discarding the organic fraction). The aqueous fraction was cooled to 0° C. and acidified with concentrated HCl. The resulting solid was filtered, washed with water and the solid dried in vacuo to afford the product (1.6 g, 70%) which was sufficiently pure to use in the subsequent step without further purification. 1H NMR (DMSO-d6) δ 8.44–8.39 (m, 2H), 7.46–7.42 (m, 2H), 7.24–7.18 (m, 2H), 6.78 (d, 1H, J=6.98 Hz), 5.31 (s, 2H); HRMS(ESI), calcd.: 248.0723, found: 248.0718.
Aufarbeitung
- concentrationThe reaction mixture was concentrated in vacuo
- additiondiluted with water
- extractionthe solution was extracted with ethyl acetate (
- filtrationThe resulting solid was filtered
- washwashed with water
- customthe solid dried in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-f0bf1cb336424f24ac8e4e0fa99e5073
- Quelldatensatz
- uspto-grants-2007_02
- Patentnummer
- US07173031B2
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