Chloroacetaldehyde → 11-Methoxyimidazo[1,2-f]phenanthridine

HRID 539493

Reaktionsgleichung

Reaktionsgleichung von HRID 539493
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:14]2[C:5](=[C:6]([NH2:17])[N:7]=[C:8]3[C:13]=2[CH:12]=[CH:11][CH:10]=[CH:9]3)[CH:4]=1.Cl[CH2:19][CH:20]=O.C(=O)(O)[O-].[Na+]>CC(O)C>[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:14]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[N:7]3[CH:19]=[CH:20][N:17]=[C:6]3[C:5]=2[CH:4]=1

Komponenten

5

Edukt 3

HCID 33ChloroacetaldehydeHCID 516892Sodium BicarbonateHCID 706543528-Methoxyphenanthridin-6-amine

Produkt 1

HCID 7065428211-Methoxyimidazo[1,2-f]phenanthridineAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

8-Methoxyphenanthridin-6-amine (0.95 g, 4.24 mmol), 2-chloroacetaldehyde (0.807 mL, 12.71 mmol), and sodium bicarbonate (1.25 g, 14.83 mmol) were added to 43 mL 2-propanol and refluxed for 15 h. After cooling to room temperature, the reaction mixture was filtered thru Celite®. After removal of the solvents, the crude material was triturated with 50 mL hexanes to give 11-methoxyimidazo[1,2-f]phenanthridine (0.99 g, 94%) as an off-white solid. The product was confirmed by GC/MS and NMR.

Aufarbeitung

  1. temperaturerefluxed for 15 h
  2. filtrationthe reaction mixture was filtered thru Celite®
  3. customAfter removal of the solvents
  4. customthe crude material was triturated with 50 mL hexanes

Quellen und Nachweise

ORD-Eintrag
ord-0da4f45d3b644d229d8223b7dd65ee48
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08871361B2

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