Acrylonitrile → HCID 69070739, Verbindung

HRID 347431Notizen

Reaktionsgleichung

[C:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:12]=1[NH:13][C:14]1[CH:19]=[CH:18][C:17](I)=[C:16]3[O:21][CH2:22][O:23][C:15]=13)=[CH:10][C:9]([O:24][CH3:25])=[C:8]([O:26][CH3:27])[CH:7]=2)#[N:2].[C:28](#[N:31])[CH:29]=[CH2:30].C(N(CC)CC)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C=O)C>[C:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:12]=1[NH:13][C:14]1[CH:19]=[CH:18][C:17]([CH:30]=[CH:29][C:28]#[N:31])=[C:16]3[O:21][CH2:22][O:23][C:15]=13)=[CH:10][C:9]([O:24][CH3:25])=[C:8]([O:26][CH3:27])[CH:7]=2)#[N:2]

Komponenten

Reaktionsbedingungen

Temperatur: 115 °C

Versuchsvorschrift

A mixture of 3-cyano-4-(4-iodo-2,3-methylenedioxyanilino)-6,7-dimethoxyquinoline (0.2 g), acrylonitrile (0.2 ml), triethylamine (0.2 ml), palladium(II) acetate (0.01 g) and DMF (2 ml) was stirred and heated to 115° C. for 3 hours. The reaction mixture was evaporated and the residue was purified by column chromatography on silica using increasingly polar mixtures of hexane and ethyl acetate as eluent. The material so obtained was triturated under diethyl ether. There was thus obtained the title compound, in the form of a 4:1 mixture of trans and cis isomers and as a yellow solid (0.095 g); NMR Spectrum: (DMSOd6, data relating to the major trans isomer) 3.91 (s, 3H), 3.93 (s, 3H), 6.12 (s, 2H), 6.26 (d, 1H), 6.88 (d, 1H), 7.14 (d, 1H), 7.35 (s, 1H), 7.56 (d, 1H), 7.7 (s, 1H), 8.51 (s, 1H), 9.7 (s, 1H); Mass Spectrum: M+H+ 401.

Aufarbeitung

customThe reaction mixture was evaporated
customthe residue was purified by column chromatography on silica using
temperatureincreasingly polar mixtures of hexane and ethyl acetate as eluent
customThe material so obtained
customwas triturated under diethyl ether

Quellen und Nachweise

ORD-Eintrag: ord-7f765a5edde44d1fa4bfeeba15e4e69c
Quelldatensatz: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07173135B2

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