Diphenyl Ether → ETHYL 4-OXO-1,4-DIHYDROPYRROLO[1,2-B]PYRIDAZINE-3-CARBOXYLATE

HRID 347471Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 347471
C1(OC2C=CC=CC=2)C=CC=CC=1.[N:14]1([NH:19][CH:20]=[C:21]([C:27]([O:29]CC)=O)[C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:18]=[CH:17][CH:16]=[CH:15]1>>[O:29]=[C:27]1[C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:20][NH:19][N:14]2[CH:15]=[CH:16][CH:17]=[C:18]12

Komponenten

3

Edukt 2

HCID 7583Diphenyl EtherHCID 10015075HCID 10015075, Verbindung

Produkt 1

HCID 10104421ETHYL 4-OXO-1,4-DIHYDROPYRROLO[1,2-B]PYRIDAZINE-3-CARBOXYLATEAusbeute 71 %

Reaktionsbedingungen

Temperatur
220 °C

Versuchsvorschrift

A mixture of N-aminopyrrole (575 mg, 7.0 mmol, commercially available) and diethyl ethoxymethylenemalonate (1.82 g, 8.4 mmol) was heated at 125° C. for 2 hours to give crude diethyl 2-((1H-pyrrol-1-ylamino)methylene)malonate. To this intermediate was added diphenyl ether (2 mL). The reaction was put under nitrogen and heated at 220° C. for 2 hours, while allowing the ethanol formed in the reaction to be distilled off. The reaction was cooled to room temperature and purified by silica gel flash chromatography (eluted with 100% CH2Cl2) to give the title compound (1.03 g, 71%) as a yellow solid.

Aufarbeitung

  1. customformed in the reaction
  2. distillationto be distilled off
  3. temperatureThe reaction was cooled to room temperature
  4. custompurified by silica gel flash chromatography (eluted with 100% CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-99fa87e0afcc4304a34620f75f7eb290
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07173031B2

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