N,N-Dimethylethylenediamine → 6-(2-dimethylaminoethyl)-4-(3-nitrophenyl)-5-oxo-2-phenyl-5,7-dihydro-(6H)-pyrrolo[3,4-b]pyridine

HRID 2106827Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2106827
Br[CH2:2][C:3]1[C:8]([C:9]([O:11]CC)=O)=[C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[CH:6]=[C:5]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:4]=1.[CH3:29][N:30]([CH3:34])[CH2:31][CH2:32][NH2:33]>C(O)(C)C>[CH3:29][N:30]([CH3:34])[CH2:31][CH2:32][N:33]1[C:9](=[O:11])[C:8]2[C:3](=[N:4][C:5]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:6][C:7]=2[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[CH2:2]1

Komponenten

4

Edukt 2

HCID 66053N,N-DimethylethylenediamineHCID 10388561Ethyl 2-bromomethyl-4-(3-nitrophenyl)-6-phenyl-3-pyridinecarboxylate

Produkt 1

HCID 103637436-(2-dimethylaminoethyl)-4-(3-nitrophenyl)-5-oxo-2-phenyl-5,7-dihydro-(6H)-pyrrolo[3,4-b]pyridineAusbeute 35,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

A mixture of ethyl 2-bromomethyl-4-(3-nitrophenyl)-6-phenyl-3-pyridinecarboxylate (1.5 g) and 2-dimethylaminoethylamine (0.6 g) is isopropyl alcohol (15 ml) was refluxed for 1 hour. The reaction mixture was evaporated in vacuo and the residue was dissolved in a mixture of water (20 ml) and chloroform (40 ml). The organic layer was washed with water and dried over magnesium sulfate. The solvent was distilled off. The residue was subjected to a column chromatography on silica gel, eluting with a mixture of chloroform and methanol (50:1 V/V). The fractions containing the desired compound were combined and evaporated in vacuo. The crystalline residue was recrystallized from ethanol to give 6-(2-dimethylaminoethyl)-4-(3-nitrophenyl)-5-oxo-2-phenyl-5,7-dihydro-(6H)-pyrrolo[3,4-b]pyridine (0.49 g).

Aufarbeitung

  1. temperaturewas refluxed for 1 hour
  2. customThe reaction mixture was evaporated in vacuo
  3. dissolutionthe residue was dissolved in a mixture of water (20 ml) and chloroform (40 ml)
  4. washThe organic layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent was distilled off
  7. washeluting with a mixture of chloroform and methanol (50:1 V/V)
  8. additionThe fractions containing the desired compound
  9. customevaporated in vacuo
  10. customThe crystalline residue was recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-3ac14c789df84ebdb5120733f721ff65
Quelldatensatz
uspto-grants-1990_06
Patentnummer
US04931453

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