Imidazole → 3-Amino-4,5-diethoxycarbonyl-6-(imidazol-1-yl)-2-phenylpyridine

HRID 37498

Reaktionsgleichung

Reaktionsgleichung von HRID 37498
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:5]([N+:18]([O-])=O)=[C:4]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:3]=1.[NH:27]1[CH:31]=[CH:30][N:29]=[CH:28]1>C(Cl)(Cl)Cl>[NH2:18][C:5]1[C:4]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[N:3][C:2]([N:27]2[CH:31]=[CH:30][N:29]=[CH:28]2)=[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:6]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Komponenten

4

Edukt 2

HCID 795ImidazoleHCID 199355872-Chloro-3,4-diethoxycarbonyl-5-nitro-6-phenylpyridine

Produkt 1

HCID 152897003-Amino-4,5-diethoxycarbonyl-6-(imidazol-1-yl)-2-phenylpyridineAusbeute 89,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A mixture of 0.379 g of 2-chloro-3,4-diethoxycarbonyl-5-nitro-6-phenylpyridine, 0.21 g of imidazole and 15 ml of chloroform was heated under reflux for 8 hours. After the reaction mixture was concentrated, the residue was extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous solution of sodium chloride and dried over sodium sulfate. After the solvent was distilled off, 5 ml of acetic acid and 0.5 g of reduced iron were added to the residue, and the mixture was stirred at room temperature for 4 hours. After an aqueous solution of sodium hydrogencarbonate was added for neutralization, extraction with ethyl acetate was conducted. The organic layer was washed with water and a saturated aqueous solution of sodium chloride and dried over sodium sulfate, followed by filtration with a small amount of silica gel. The filtrate was concentrated under reduced pressure, to give 0.342 g of the title compound as a yellow oily substance.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder reflux for 8 hours
  3. concentrationAfter the reaction mixture was concentrated
  4. extractionthe residue was extracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materiala saturated aqueous solution of sodium chloride and dried over sodium sulfate
  7. distillationAfter the solvent was distilled off
  8. addition5 ml of acetic acid and 0.5 g of reduced iron were added to the residue
  9. additionAfter an aqueous solution of sodium hydrogencarbonate was added for neutralization, extraction with ethyl acetate
  10. washThe organic layer was washed with water
  11. dry with materiala saturated aqueous solution of sodium chloride and dried over sodium sulfate
  12. filtrationfollowed by filtration with a small amount of silica gel
  13. concentrationThe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-78b21301283c45709220707c2c207948
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05420275

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