Pyridine → Methyl 4-(1-dimethylaminomethylene-2-oxopentyl)-3-nitrobenzoate

HRID 1108702

Reaktionsgleichung

[CH3:1][N:2]([CH3:18])/[CH:3]=[CH:4]/[C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][C:6]=1[N+:15]([O-:17])=[O:16].N1C=CC=CC=1.[C:25](Cl)(=[O:29])[CH2:26][CH2:27][CH3:28]>O1CCCC1.O>[CH3:18][N:2]([CH:3]=[C:4]([C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][C:6]=1[N+:15]([O-:17])=[O:16])[C:25](=[O:29])[CH2:26][CH2:27][CH3:28])[CH3:1]

Komponenten

Reaktionsbedingungen

Temperatur: 50 °C

Versuchsvorschrift

To a stirred mixture of methyl (E)-4-[2-(dimethylamino)vinyl]-3-nitrobenzoate (500 mg), which was prepared by the method of Brown et al. described in Journal of Medicinal Chemistry, vol. 35, page 2419 (1992), and pyridine (0.16 ml) in tetrahydrofuran (3 ml) was added butyryl chloride (0.21 ml) at 20° C. The reaction mixture was stirred at 40° C. for 24 hours and 50° C. for 4 hours. After cooled to 20° C., the reaction mixture was diluted with water and extracted with ethyl acetate. The organic phase was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel eluting with a mixture of ethyl acetate and hexane (1:1) to give methyl 4-(1-dimethylaminomethylene-2-oxopentyl)-3-nitrobenzoate (426 mg) as colorless amorphous.

Aufarbeitung

customwas prepared by the method of Brown et al.
temperatureAfter cooled to 20° C.
extractionextracted with ethyl acetate
washThe organic phase was washed with water and brine
dry with materialdried over magnesium sulfate
customevaporated in vacuo
customThe residue was chromatographed on silica gel eluting with a mixture of ethyl acetate and hexane (1:1)

Quellen und Nachweise

ORD-Eintrag: ord-1fcbf5fece15453f9a552fa4c964373e
Quelldatensatz: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06069156

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