Methylamine → Ethyl 4-hydroxy-1,2,5-trimethyl-6-oxo-1,6-dihydropyridine-3-carboxylate

HRID 421871

Reaktionsgleichung

C(O[C:4](=[O:15])[CH:5]([CH3:14])[C:6](=[O:13])[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])C.C(OC(O[CH2:22][CH3:23])=C)C.[CH3:24][NH2:25]>C(OCC)C.C[O-].[Na+]>[CH2:11]([O:10][C:8]([C:7]1[C:6]([OH:13])=[C:5]([CH3:14])[C:4](=[O:15])[N:25]([CH3:24])[C:22]=1[CH3:23])=[O:9])[CH3:12]

Komponenten

Reaktionsbedingungen

Temperatur: 85 °C

Versuchsvorschrift

A mixture of 2-methyl-3-oxo-pentanedioic acid diethyl ester (10.0 g, 46.3 mmol), 1,1-diethoxy-ethene (12.8 mL, 92.5 mmol) and sodium methoxide (0.026 mg, 0.481 mmol) was heated to 85° C. for nine hours. The reaction mixture was cooled to room temperature and concentrated. To the resulting residue was added methylamine (1.91 mL, 55.5 mmol, 40% H2O). After stirring at room temperature for 16 hours, the reaction mixture was diluted with diethyl ether and washed with water. The aqueous phase was acidified to pH 1 with 10% HCl solution and extracted with EtOAc. The organic layer was dried (MgSO4) and concentrated. Trituration of the resulting residue with diethyl ether and flash column chromatography (3% MeOH in methylene chloride) gave 3.55 g (34%) desired product.

Aufarbeitung

temperatureThe reaction mixture was cooled to room temperature
concentrationconcentrated
washwashed with water
extractionextracted with EtOAc
dry with materialThe organic layer was dried (MgSO4)
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-bc7d628608d441a2be9d34b0a3cd5106
Quelldatensatz: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08101611B2

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