Hydrochloric Acid → 4-acetyl-1-methyl-5-(1-oxo-2,3-dihydro-1H-inden-5-yl)-1H-pyrrole-2-carbonitrile

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Reaktionsgleichung

[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[C:12](=[O:16])[CH2:11][CH2:10]3)=[CH:5][CH:4]=[C:3]1[C:17]#[N:18].[I-].[Sm+3].[I-].[I-].[C:23](Cl)(=[O:25])[CH3:24].Cl>C(#N)C>[C:23]([C:5]1[CH:4]=[C:3]([C:17]#[N:18])[N:2]([CH3:1])[C:6]=1[C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[CH2:11][CH2:10]2)(=[O:25])[CH3:24]

Komponenten

Reaktionsbedingungen

Temperatur: 120 °C

Versuchsvorschrift

To a stirred solution of 1-methyl-5-(1-oxo-2,3-dihydro-1H-inden-5-yl)-1H-pyrrole-2-carbonitrile (0.25 g, 1.0 mmol) in acetonitrile (25 mL) was added samarium iodide (0.5 g, 1.2 mmol) and acetyl chloride (1.75 mL, 24.6 mmol). The reaction mixture was heated in microwave to 120° C. for 10 minutes. The mixture was treated with a 10% aqueous HCl solution (50 mL) and extracted with ethyl acetate (3×50 mL). The organic layers were combined, dried over magnesium sulfate, filtered, and concentrated. The residue was purified on a silica gel column (30% ethyl acetate in hexane) to give 4-acetyl-1-methyl-5-(1-oxo-2,3-dihydro-1H-inden-5-yl)-1H-pyrrole-2-carbonitrile as a tan solid (0.025 g, 8%). MS (ESI) m/z 279; HRMS: calcd for C17H14N2O2+H+, 279.1128; found (ESI, [M+H]+), 279.1125.

Aufarbeitung

extractionextracted with ethyl acetate (3×50 mL)
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated
customThe residue was purified on a silica gel column (30% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag: ord-8bf401ec560c4ccc93e2760da1f40ff4
Quelldatensatz: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07319152B2

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