N-methyl-2-pyrrolidone → 1-(3-Methoxy-4-nitrophenylamino)-2-methylpropan-2-ol

HRID 42268

Reaktionsgleichung

F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([O:11][CH3:12])[CH:3]=1.[NH2:13][CH2:14][C:15]([CH3:18])([OH:17])[CH3:16].CN1CCCC1=O.CCN(C(C)C)C(C)C>O>[CH3:12][O:11][C:4]1[CH:3]=[C:2]([NH:13][CH2:14][C:15]([CH3:18])([OH:17])[CH3:16])[CH:7]=[CH:6][C:5]=1[N+:8]([O-:10])=[O:9]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

A 20 mL reaction vial equipped with a stir bar was charged with 4-fluoro-2-methoxy-1-nitrobenzene (0.5 g, 2.92 mmol), 1-amino-2-methylpropan-2-ol (0.313 g, 3.51 mmol), N-methyl-2-pyrrolidinone (7.3 mL) and Hunig's base (N,N-diisopropylethylamine) (0.76 g, 5.84 mmol). The vessel was sealed and the reaction was heated on a thermal block at 80° C. for 24 hours. The reaction was cooled to ambient temperature, treated with water (40 mL) and extracted with ethyl acetate (3×60 mL). The combined organic layers were washed with brine (25 mL), dried over Na2SO4, filtered, and concentrated. The concentrate was purified by flash chromatography on a 10 g silica gel column with 1% methanol/CH2Cl2 to provide the title compound.

Aufarbeitung

customA 20 mL reaction
customvial equipped with a stir bar
customThe vessel was sealed
temperatureThe reaction was cooled to ambient temperature
extractionextracted with ethyl acetate (3×60 mL)
washThe combined organic layers were washed with brine (25 mL)
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe concentrate was purified by flash chromatography on a 10 g silica gel column with 1% methanol/CH2Cl2

Quellen und Nachweise

ORD-Eintrag: ord-c98108077fe4464e8dc39edb59beb0a9
Quelldatensatz: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08536180B2

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