Butylamine → Methyl 3-(butylamino)-4-nitrobenzoate

HRID 14197

Reaktionsgleichung

C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:53]([NH2:57])[CH2:54][CH2:55][CH3:56].[N+:58]([C:61]1[CH:70]=[CH:69][C:64]([C:65]([O:67][CH3:68])=[O:66])=[CH:63][C:62]=1OS(C(F)(F)F)(=O)=O)([O-:60])=[O:59]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:53]([NH:57][C:70]1[CH:69]=[C:64]([CH:63]=[CH:62][C:61]=1[N+:58]([O-:60])=[O:59])[C:65]([O:67][CH3:68])=[O:66])[CH2:54][CH2:55][CH3:56]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

To a stirred solution of Pd2(dba)3 (139 mg), BINAP (284 mg), and cesium carbonate (2.0 g) in toluene (50 mL) was added butylamine (0.45 mL), and the reaction mixture was heated at 80° C. for 15 min. A solution of methyl 4-nitro-3-{[(trifluoromethyl)sulfonyl]oxy}benzoate (1.0 g) in toluene (15 mL) was added dropwise over 1 h. The mixture was cooled to room temperature, filtered through diatomaceous earth, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 3:1 ethyl acetate/hexanes) provided 670 mg of the title compound as a yellow oil: ESI MS m/z 550 [M+H]+.

Aufarbeitung

temperatureThe mixture was cooled to room temperature
filtrationfiltered through diatomaceous earth
concentrationconcentrated under reduced pressure
customPurification by flash column chromatography (silica, 3:1 ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag: ord-20e5585ebb224339ae4db3c764c1d80e
Quelldatensatz: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07727997B2

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