Pyrrolidine → HCID 136463775, Verbindung

HRID 862102

Reaktionsgleichung

Reaktionsgleichung von HRID 862102
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:21])=[C:6]([CH:20]=1)[C:7]([C:9]1[C:14]([CH:15]2[O:19][CH2:18][CH2:17][O:16]2)=[CH:13][CH:12]=[CH:11][N:10]=1)=O.Cl.[C:23]([O:27][NH2:28])([CH3:26])([CH3:25])[CH3:24].N1CCCC1>C(O)CC>[C:23]([O:27]/[N:28]=[C:7](\[C:9]1[C:14]([CH:15]2[O:19][CH2:18][CH2:17][O:16]2)=[CH:13][CH:12]=[CH:11][N:10]=1)/[C:6]1[CH:20]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=1[OH:21])([CH3:26])([CH3:25])[CH3:24]

Komponenten

5

Edukt 3

HCID 31268PyrrolidineHCID 2777906O-tert-butylhydroxylamine hydrochlorideHCID 197016352-(5-Bromo-2-hydroxybenzoyl)-3-(1,3-dioxolan-2-yl)pyridine

Produkt 1

HCID 136463775HCID 136463775, VerbindungAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 10311-PropanolLösungsmittel

Versuchsvorschrift

A solution of 2-(5-bromo-2-hydroxybenzoyl)-3-(1,3-dioxolan-2-yl)pyridine (2.92 g), O-t-butyl-hydroxylamine hydrochloride (2.09 g) and pyrrolidine (1.78 g) in n-propanol (40 ml) was heated for 2 hours under reflux. The reaction mixture was concentrated, to which was added water, followed by subjecting the mixture to extraction with ethyl acetate. The extract solution was washed with a saturated aqueous saline solution, dried (anhydrous sodium sulfate), and concentrated. The concentrate was purified by means of a silica gel column chromatography (eluent: ethyl acetate/hexane) to give (Z)-2-(5-bromo-2-hydroxybenzoyl)-3-(1,3-dioxolan-2-yl)pyridine O-t-butyloxime (2.81 g) (Compound 134).

Aufarbeitung

  1. temperatureunder reflux
  2. concentrationThe reaction mixture was concentrated, to which
  3. additionwas added water
  4. extractionto extraction with ethyl acetate
  5. washThe extract solution was washed with a saturated aqueous saline solution
  6. dry with materialdried (anhydrous sodium sulfate)
  7. concentrationconcentrated
  8. customThe concentrate was purified by means of a silica gel column chromatography (eluent: ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-a0acd65784ad4ce680a9cb519443478b
Quelldatensatz
uspto-grants-1998_02
Patentnummer
US05716971

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