Dimethylacetamide → HCID 17980587, Verbindung

HRID 1784105Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1784105
[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[C:29]([N:31](C)C)=O>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].C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[CH-]1C=CC=C1.[Fe+2].[Zn]>[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]([C:29]#[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

6

Edukt 2

HCID 31374DimethylacetamideHCID 10310906HCID 10310906, Verbindung

Produkt 1

HCID 17980587HCID 17980587, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23994ZincKatalysatorHCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 15826098Cyclopenta-1,3-diene;cyclopenta-2,4-dien-1-yl(diphenyl)phosphane;iron(2+)Katalysator

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

Tris(dibenzylideneacetone)dipalladium (0.0073 g) was added to a mixture of 3-cyano-4-(4-iodo-2,3methylenedioxyanilino)-6,7-dimethoxyquinoline (0.05 g) zinc cyanide (0.015 g), diphenylphosphinoferrocene (0.009 g), zinc powder (0.0035 g) and DMA (2 ml) and the resultant mixture was stirred and heated to 110° C. for 1 hour. The mixture was cooled to ambient temperature and partitioned between ethyl acetate and water. The organic layer was dried over magnesium sulphate and 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 3-cyano-4-(4-cyano-2,3-methylenedioxyamino)-6.7-dimethoxyquinoline as a solid (0.014 g); NMR Spectrum: (CDCl3) 3.84 (s, 3H), 4.07 (s, 3H), 6.16 (s, 2H), 6.28 (d, 1H), 6.75 (s, 1H), 6.99 (m, 2H), 7.46 (s, 1H), 8.73 (s, 1H); Mass Spectrum: M+H+ 375.

Aufarbeitung

  1. temperatureThe mixture was cooled to ambient temperature
  2. custompartitioned between ethyl acetate and water
  3. dry with materialThe organic layer was dried over magnesium sulphate
  4. customevaporated
  5. customthe residue was purified by column chromatography on silica using
  6. temperatureincreasingly polar mixtures of hexane and ethyl acetate as eluent
  7. customThe material so obtained
  8. customwas triturated under diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-3184a89c183a481bbd9ff639d1b3d240
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07501516B2

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