Dimethylformamide → HCID 54112325, Verbindung

HRID 1678134Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1678134
P(Cl)(Cl)(Cl)=O.[CH3:6][N:7](C)[CH:8]=[O:9].[C:11]1([N:17]2[C:21]3=[N:22][CH:23]=[CH:24][CH:25]=[C:20]3[CH2:19][C:18]2=O)C=CC=CC=1.[OH-].[NH4+]>O.ClCCl.N1C=CC=CC=1>[CH3:11][N:17]([CH:18]=[C:19]1[C:20]2[C:6](=[N:22][CH:23]=[CH:24][CH:25]=2)[NH:7][C:8]1=[O:9])[CH3:21]

Komponenten

8

Edukt 4

HCID 6228DimethylformamideHCID 14923Ammonium HydroxideHCID 24813Phosphorus oxychlorideHCID 149872061-Phenyl-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one

Produkt 1

HCID 54112325HCID 54112325, VerbindungAusbeute 47,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 1049PyridineLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
2.5 °C

Versuchsvorschrift

Phosphorous oxychloride (693 μL, 7.47 mmol) is added slowly to a stirred solution of dimethylformamide (714 μL) and dichloromethane (714 μL) cooled to 0-5° C. After 10 min, a solution of the above 1-phenyl-1,3-dihydropyrrolo[2,3-b]pyridin-2-one (350 mg, 1.66 mmol), pyridine (357 μL) and dichloromethane (1.43 mL) is added and the reaction is stirred at room temperature for 24 hr. The reaction mixture is poured into water, the pH adjusted to 8 with ammonium hydroxide and extracted with dichloromethane (2×). The combined extract is dried, filtered and concentrated. The residue is purified by chromatography eluting with dichlormethane-2% methanol. Product containing fractions are combined and concentrated to afford 3-dimethylaminomethylene-1,3-dihydropyrrolo[2,3-b]pyridin-2-one (211 mg, 47.9% yield).

Aufarbeitung

  1. extractionextracted with dichloromethane (2×)
  2. extractionThe combined extract
  3. customis dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is purified by chromatography
  7. washeluting with dichlormethane-2% methanol
  8. additionProduct containing fractions
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-df616151b4a6439eb20dc84a62eb1dc7
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08008491B2

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