Reaktionsgleichung
C([O:8][C:9]1[C:10](=[O:16])[CH:11]=[C:12]([CH3:15])[NH:13][CH:14]=1)C1C=CC=CC=1.[H][H].[ClH:19]>CO.O.[Pd]>[ClH:19].[OH:8][C:9]1[C:10](=[O:16])[CH:11]=[C:12]([CH3:15])[NH:13][CH:14]=1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Versuchsvorschrift
5-Benzyloxy-2-methyl-1H-pyridin-4-one (15.5 g, 72.0 mmol) was mixed with 10% Pd/C (1.60 g) in methanol (200 mL) and water (35 mL) in a Parr hydrogenator bottle. The mixture was hydrogenated on a Parr hydrogenator for 45 minutes at 50 psi hydrogen pressure. 6N HCl (12 mL) was added. A CELITE™ bed was prepared on a sintered glass, and washed with 6M HCl (100 mL), followed by water (7×50 mL) and then methanol (2×50 mL) under suction. The reaction mixture was filtered through the pre-treated CELITE™ bed. The filtrate was evaporated to dryness and the residue was triturated with acetone, then filtered to give 5-hydroxy-2-methyl-1H-pyridin-4-one hydrochloride 9.30 g as off-white solid. The mother liquor was diluted with hexane and placed at room temperature over night to give an additional 1.63 g of product. Thus, 10.9 g of the title compound was obtained (94% yield). 1H NMR (90 MHz, MeOD) δ (ppm) 7.93 (s, 1H, CH), 7.07 (s, 1H, CH) 2.56 (s, 3H, CH3,). MS-ESI (m/z): 126.1 [M+1]+, 108.2, 110.1.
Aufarbeitung
- customA CELITE™ bed was prepared on a sintered glass
- washwashed with 6M HCl (100 mL)
- filtrationThe reaction mixture was filtered through the pre-treated CELITE™ bed
- customThe filtrate was evaporated to dryness
- customthe residue was triturated with acetone
- filtrationfiltered
Quellen und Nachweise
- ORD-Eintrag
- ord-9deddefef1914619894e93d00aace4dd
- Quelldatensatz
- uspto-grants-2011_09
- Patentnummer
- US08026261B2
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