4-Pyridineacetic acid hydrochloride → HCID 18780247, Verbindung

HRID 345698

Reaktionsgleichung

Reaktionsgleichung von HRID 345698
Cl.[N:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[CH:12]([N:15]([CH:18]([CH3:20])[CH3:19])[CH2:16][CH3:17])(C)C>ClCCl>[CH3:12][N:15]1[C:18]2[C:20](=[CH:3][CH:4]=[CH:5][CH:19]=2)[C:17]([C:8]2[C:9](=[O:10])[O:10][C:9](=[O:11])[C:8]=2[C:5]2[CH:6]=[CH:7][N:2]=[CH:3][CH:4]=2)=[CH:16]1

Komponenten

4

Edukt 2

HCID 810974-Pyridineacetic acid hydrochlorideHCID 81531Diisopropylethylamine2×

Produkt 1

HCID 18780247HCID 18780247, VerbindungAusbeute 21,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

5 g of 4-pyridyl-acetic acid hydrochloride and 3.72 g of diisopropylethylamine in 50 ml of dichloromethane were treated at 0° C. firstly with 6.37 g of 1-methylindole-3-glyoxylyl chloride in 50 ml of dichloromethane and then with 7.5 g of diisopropylethylamine. The mixture was allowed to warm to room temperature and was then stirred for 65 hours. The solvent was removed under reduced pressure and the residue was taken up in dichloromethane and chromatographed on silica gel with ethyl acetate. The product-containing fractions were concentrated. Crystallization from ethyl acetate/hexane yielded 940 mg of 3-(1-methyl-3-indolyl)-4-(4-pyridyl)furan-2,5-dione, m.p. 217°-219° C.

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. customchromatographed on silica gel with ethyl acetate
  3. concentrationThe product-containing fractions were concentrated
  4. customCrystallization from ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-cefa521c988b459f8532c75ce1a6145a
Quelldatensatz
uspto-grants-1991_10
Patentnummer
US05057614

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