Hydrochloric Acid → HCID 59463399, Verbindung

HRID 1712967Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1712967
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH3:10][C:11]1[N:12]([C:17]2[N:22]=[CH:21][C:20]([C:23](=[O:25])[CH3:24])=[CH:19][CH:18]=2)[C:13]([CH3:16])=[CH:14][CH:15]=1.Cl>[OH-].[Na+].CCO>[CH3:10][C:11]1[N:12]([C:17]2[N:22]=[CH:21][C:20]([C:23](=[O:25])/[CH:24]=[CH:4]/[C:3]3[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=3[OH:1])=[CH:19][CH:18]=2)[C:13]([CH3:16])=[CH:14][CH:15]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 6998SalicylaldehydeHCID 534030171-[6-(2,5-Dimethyl-1H-pyrrol-1-yl)pyridin-3-yl]ethan-1-one

Produkt 1

HCID 59463399HCID 59463399, VerbindungAusbeute 36 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittel2×HCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

To a vigorously stirred solution of 2-hydroxybenzaldehyde in 2.5N NaOH (2.2 mL) at 0° C. was added 1-[6-(2,5-dimethyl-1H-pyrrol-1-yl)pyridin-3-yl]ethanone (prepared by a method analogous to that described by Scott et al., Org. Proc. Res. And Dev., 8:587 (2004)) (0.58 g, 2.7 mmol) in EtOH (2 mL). The reaction mixture was allowed to stir and warm to rt whereupon an additional 1 mL of EtOH was added. The mixture turned a dark red color and was allowed to stir for 25 h. The reaction was neutralized by the addition of 1M HCl and the mixture was extracted with EtOAc. The organic solutions were combined, dried over MgSO4, filtered, and concentrated. The residue was purified by column chromatography to give (2E)-1-[6-(2,5-dimethyl-1H-pyrrol-1-yl)pyridin-3-yl]-3-(2-hydroxyphenyl)prop-2-en-1-one as a yellow solid (0.31 g, 36%). LCMS: (FA) ES+ 319.2 (M+1).

Aufarbeitung

  1. customprepared by a method analogous to
  2. additionwas added
  3. stirringto stir for 25 h
  4. extractionthe mixture was extracted with EtOAc
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-1a8bbac8606045d089ff52ca56108b18
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07795249B2

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