Hydrochloric Acid → 2-Methyl-N-[4-[(5(6H)-phenanthridinyl)carbonyl]phenyl]benzamide

HRID 355881

Reaktionsgleichung

Reaktionsgleichung von HRID 355881
[CH:1]1[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:7][NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH3:15][C:16]1[CH:33]=[CH:32][CH:31]=[CH:30][C:17]=1[C:18]([NH:20][C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][CH:22]=1)=[O:19].Cl>N1C=CC=CC=1>[CH3:15][C:16]1[CH:33]=[CH:32][CH:31]=[CH:30][C:17]=1[C:18]([NH:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([N:6]2[CH2:7][C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:14]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]2=3)=[O:26])=[CH:23][CH:22]=1)=[O:19]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 2199665,6-DihydrophenanthridineHCID 107074414-[(2-methylbenzoyl)amino]benzoyl Chloride

Produkt 1

HCID 153079712-Methyl-N-[4-[(5(6H)-phenanthridinyl)carbonyl]phenyl]benzamideAusbeute 18,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a solution of 0.181 g (1.0 mmol) of 5,6-dihydrophenanthridine in 2 ml of warm pyridine is added 0.273 g (1.0 mmol) of 4-[(2-methylbenzoyl)amino]benzoyl chloride. The mixture is stirred overnight at room temperature, 1.2 ml of 2N HCl added. The solid which separates is filtered and washed with water. The solid is dissolved in dichloromethane and the solution washed with 2M sodium carbonate. The organic layer is concentrated and the residue chromatographed twice on silica gel with ethyl acetate-hexane as solvent to give 79 mg of crystals, m.p. 190°-194° C. Mass Spec-FAB 419 (M+H).

Aufarbeitung

  1. filtrationThe solid which separates is filtered
  2. washwashed with water
  3. dissolutionThe solid is dissolved in dichloromethane
  4. washthe solution washed with 2M sodium carbonate
  5. concentrationThe organic layer is concentrated
  6. customthe residue chromatographed twice on silica gel with ethyl acetate-hexane as solvent

Quellen und Nachweise

ORD-Eintrag
ord-b000c40d0618487785d1a1af9cf847b7
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05834461

Verknüpfte Notizen

Wird geladen…