Nitrogen → 4-Acridinecarboxamide

HRID 1873068

Reaktionsgleichung

Reaktionsgleichung von HRID 1873068
[CH:1]1[C:14]2[C:5](=[N:6][C:7]3[C:12]([CH:13]=2)=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:4]([C:15]([O:17]C)=O)=[CH:3][CH:2]=1.C[N:20](C)CCN.N#N>C(O)CC>[CH:1]1[C:14]2[C:5](=[N:6][C:7]3[C:12]([CH:13]=2)=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:4]([C:15]([NH2:20])=[O:17])=[CH:3][CH:2]=1

Komponenten

5

Edukt 3

HCID 947NitrogenHCID 66053N,N-DimethylethylenediamineHCID 11064418Methyl Acridine-4-carboxylate

Produkt 1

HCID 30257214-AcridinecarboxamideAusbeute 80,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 10311-PropanolLösungsmittel

Versuchsvorschrift

A solution of 8a (1.83 g, 7.72 mmol) and N,N-dimethylethylenediamine (3.40 g, 38.6 mmol) in propan-1-ol (80 ml) was flushed with N2, and the mixture was heated at reflux for three days under N2. Solvent was then removed under reduced pressure, and the residue was partitioned between CH2Cl2 (100 ml) and 1M Na2CO3 (100 ml). The organic layer was evaporated and the residue chromatographed on alumina, eluting with CH2Cl2 /MeOH (199:1) to give N-[2-dimethylamino)ethyl]acridine-4-carboxamide 3a (1.38 g, 61%), mp (diHCl salt) 191-195° C., identical with an authentic sample.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureat reflux for three days under N2
  3. customSolvent was then removed under reduced pressure
  4. customthe residue was partitioned between CH2Cl2 (100 ml) and 1M Na2CO3 (100 ml)
  5. customThe organic layer was evaporated
  6. customthe residue chromatographed on alumina
  7. washeluting with CH2Cl2 /MeOH (199:1)

Quellen und Nachweise

ORD-Eintrag
ord-d24154741994496ab7f5e21c1358a191
Quelldatensatz
uspto-grants-2000_08
Patentnummer
US06111109

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