Citric Acid → 3,4,5-Trimethoxy-N-methycinnamohydroxamic acid

HRID 620404

Reaktionsgleichung

C(N(CC)CC)C.[CH3:8][O:9][C:10]1[CH:11]=[C:12]([CH:18]=[C:19]([O:23][CH3:24])[C:20]=1[O:21][CH3:22])[CH:13]=[CH:14][C:15](O)=[O:16].ClC(OCC)=O.Cl.[CH3:32][NH:33][OH:34].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C)C=O>[CH3:8][O:9][C:10]1[CH:11]=[C:12]([CH:18]=[C:19]([O:23][CH3:24])[C:20]=1[O:21][CH3:22])[CH:13]=[CH:14][C:15]([N:33]([CH3:32])[OH:34])=[O:16]

Komponenten

Reaktionsbedingungen

Temperatur: -12 °C

Versuchsvorschrift

Triethylamine (3.07 ml, 22 mmol) was added to a stirred solution of 3,4,5-trimethoxycinnamic acid (4.76 g, 20 mmol) in N,N-dimethylformamide (30 ml). The resulting solution was cooled to -12° C., and ethyl chloroformate (2.00 ml, 21 mmol) was added dropwise with stirring. After 15 minutes, solid N-methylhydroxylamine hydrochloride (1.84 g, 22 mmol) was added, followed by triethylamine (3.2 ml, 23 mmol). The mixture was allowed to warm to room temperature, stirred overnight, and poured into 150 ml of 1% aqueous citric acid. The mixture was extracted twice with ethyl ether, and the combined extracts washed successively with water and brine, then dried over MgSO4, filtered, and evaporated. The residue was recrystallized from ethyl acetate to provide 1.82 g (34% yield) of the titled compound as colorless crystals, mp 169°-170° C.

Aufarbeitung

temperatureto warm to room temperature
stirringstirred overnight
extractionThe mixture was extracted twice with ethyl ether
washthe combined extracts washed successively with water and brine
dry with materialdried over MgSO4
filtrationfiltered
customevaporated
customThe residue was recrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag: ord-3701ffc56a7f42ecb653d82459bf55ba
Quelldatensatz: uspto-grants-1989_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04820828

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