Methyl iodide → HCID 20039734, Verbindung

HRID 1762809Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1762809
[CH:1]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:2]=1[CH2:3][C:4]1[N:5]([CH:11]=[C:12]3[C:17]=1[C:16](=[O:18])[C:15]1[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=1[C:13]3=[O:23])[CH2:6]2.[C:24](=O)([O-])[O-].[K+].[K+].IC>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(#N)C.ClCCl>[CH3:24][CH:3]1[C:2]2[C:7](=[CH:8][CH:9]=[CH:10][CH:1]=2)[CH2:6][N:5]2[CH:11]=[C:12]3[C:17]([C:16](=[O:18])[C:15]4[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=4[C:13]3=[O:23])=[C:4]12

Komponenten

7

Edukt 3

HCID 6328Methyl iodide2×HCID 11430Potassium CarbonateHCID 71772Mitoquidone2×

Produkt 1

HCID 20039734HCID 20039734, VerbindungAusbeute 9,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 66133Benzyl triethylammonium chlorideKatalysatorHCID 6342AcetonitrileLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 5,14-dihydrobenz[5,6]isoindolo[2,1-b]isoquinoline-8,13-dione (0.96 g) (Intermediate 1), benzyl triethylammonium chloride (0.16 g), potassium carbonate (2.20 g) and iodomethane (0.45 ml) in acetonitrile (100 ml) was stirred and heated under reflux for 4 h. A further portion of iodomethane (0.5 ml) was added and the mixture was stirred at 80° C. for 1 h. The mixture was cooled to room temperature, diluted with dichloromethane (250 ml) and filtered. The filtrate was concentrated in vacuo and the residue was purified on preparative plates eluting five times with chloroform to give the title compound (98 mg) m.p. 215°-218° C. λmax (in CHCl3) 246.5 nm (ε51,050), 266.5 nm (ε18,250) and 366.55 nm (ε3,700).

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux for 4 h
  3. stirringthe mixture was stirred at 80° C. for 1 h
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue was purified on preparative plates
  7. washeluting five times with chloroform

Quellen und Nachweise

ORD-Eintrag
ord-840537cf7f7a408c894e6692af625f16
Quelldatensatz
uspto-grants-1989_05
Patentnummer
US04835158

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