Dichloromethane → 1-(2-Methylphenyl)-6-methylpyrrolo[3,2-c]cinnoline

HRID 704573

Reaktionsgleichung

Reaktionsgleichung von HRID 704573
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:20]2[C:19]3[CH:18]=[CH:17][CH:16]=[C:15]([CH3:21])[C:14]=3[N:13]=[N:12][C:11]=2[CH2:10][CH2:9]1.ClCCl>C1(OC2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)Cl.[Pd]>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:20]2[C:19]3[CH:18]=[CH:17][CH:16]=[C:15]([CH3:21])[C:14]=3[N:13]=[N:12][C:11]=2[CH:10]=[CH:9]1

Komponenten

6

Edukt 2

HCID 6344DichloromethaneHCID 200727571-(2-Methylphenyl)-6-methyl-2,3-dihydropyrrolo [3,2-c]cinnoline

Produkt 1

HCID 200727541-(2-Methylphenyl)-6-methylpyrrolo[3,2-c]cinnoline

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 6212ChloroformLösungsmittel2×HCID 7583Diphenyl EtherLösungsmittel

Versuchsvorschrift

To a refluxing slurry of 10% Pd/C (0.4 g) in diphenyl ether (20 ml) was added 1-(2-methylphenyl)-6-methyl-2,3-dihydropyrrolo [3,2-c]cinnoline (1.25 g, 0.0045 mol). After 0.5 hour at reflux temperature the reaction mixture was cooled, diluted with chloroform and the catalyst was filtered off over hyflo. The product was isolated by column chromatography using dichloromethane (11) then chloroform. The oil obtained was crystallized from ethyl acetate, 0.42 g, m.p. 105-106°.

Aufarbeitung

  1. temperatureAfter 0.5 hour at reflux temperature the reaction mixture
  2. temperaturewas cooled
  3. filtrationthe catalyst was filtered off over hyflo
  4. customThe product was isolated by column chromatography
  5. customThe oil obtained
  6. customwas crystallized from ethyl acetate, 0.42 g, m.p. 105-106°

Quellen und Nachweise

ORD-Eintrag
ord-c6ddbe0469dc4c2e99913a8c9ed2a0f2
Quelldatensatz
uspto-grants-1991_01
Patentnummer
US04988695

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