3-Benzyloxy-6-methyl-4-oxo-1,4-dihydro-pyridine-2-carboxylic acid → 5-(benzyloxy)-2-methylpyridin-4(1H)-one

HRID 913040

Reaktionsgleichung

[CH2:1]([O:8][C:9]1[C:14](=[O:15])[CH:13]=[C:12]([CH3:16])[NH:11][C:10]=1C(O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CN(C)C=O>[CH2:1]([O:8][C:9]1[C:14](=[O:15])[CH:13]=[C:12]([CH3:16])[NH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

Reaktionsbedingungen

Temperatur: 120 °C

Versuchsvorschrift

A mixture of 3-benzyloxy-6-methyl-4-oxo-1,4-dihydro-pyridine-2-carboxylic acid (5.2 g, 20.0 mmol) in dimethylformamide (12 mL) was heated in an oil bath for 8 h. The temperature of the oil bath was maintained at 120° C. A solid separated upon cooling to RT. The solid 5-benzyloxy-2-methyl-1H-pyridin-4-one was suction filtered and washed with hexane. The isolated solid was dried under high vacuum for 16 h (3.32 g, 77% yield). 1H NMR (400 MHz, MeOH-D4) δ (ppm): 7.45-7.46 (m, overlapping peaks, 2H, Ar—H and CH), 7.29-7.39 (m, overlapping peaks, 4H, Ar—H), 6.34 (s, 1H, CH), 5.07 (s, 2H, OCH2), 2.30 (s, 3H, CH3); MS-ESI (m/z): 216.3 [M+1]+, 215.6 [M]+, 188.3.

Aufarbeitung

temperaturewas heated in an oil bath for 8 h
customA solid separated
temperatureupon cooling to RT
filtrationfiltered
washwashed with hexane
customThe isolated solid was dried under high vacuum for 16 h (3.32 g, 77% yield)

Quellen und Nachweise

ORD-Eintrag: ord-2e80d71a5ed84d8fbe89bdeb7b434d19
Quelldatensatz: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08026261B2

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