Ammonium Chloride → 1-oxo-3-phenyl-6-(3-phenylpropoxy)-1H-indene-2-carbonitrile

HRID 17889

Reaktionsgleichung

Br[C:2]1[C:3](=[O:27])[C:4]2[C:9]([C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[CH:8][CH:7]=[C:6]([O:17][CH2:18][CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH:5]=2.[Cu][C:29]#[N:30].[Cl-].[NH4+]>CN(C)C=O>[O:27]=[C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[C:6]([O:17][CH2:18][CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:5]=2)[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:2]1[C:29]#[N:30]

Komponenten

Reaktionsbedingungen

Temperatur: 150 °C

Versuchsvorschrift

2-Bromo-3-phenyl-6-(3-phenylpropoxy)indene-1-one (1.0 g, 2.3 mmol) was dissolved in N,N-dimethylformamide (10 ml). Copper (I) cyanide (617 mg, 6.9 mmol) was added thereto and the mixture was stirred for 3 hours at 150° C. The mixture was cooled, and saturated ammonium chloride was added thereto. The organic layer was extracted with ethyl acetate, dried over anhydrous magnesium sulfate, concentrated, and the resulting residue was purified by column chromatography (ethyl acetate:hexane=1:3) to obtain the title compound (700 mg, yield 80%) as a red solid.

Aufarbeitung

temperatureThe mixture was cooled
extractionThe organic layer was extracted with ethyl acetate
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated
customthe resulting residue was purified by column chromatography (ethyl acetate:hexane=1:3)

Quellen und Nachweise

ORD-Eintrag: ord-be4c3fb850964b1bb1e28c3c67e9cbba
Quelldatensatz: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07741323B2

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