Pyridine → Ethyl 3-hydroxyimino-5-methoxy-1-phenylindene-2-carboxylate

HRID 19549

Reaktionsgleichung

Reaktionsgleichung von HRID 19549
[CH2:1]([O:3][C:4]([C:6]1[C:7](=O)[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][CH:11]=[C:10]([O:21][CH3:22])[CH:9]=2)=[O:5])[CH3:2].Cl.[NH2:25][OH:26].N1C=CC=CC=1>C(O)C>[CH2:1]([O:3][C:4]([C:6]1[C:7](=[N:25][OH:26])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][CH:11]=[C:10]([O:21][CH3:22])[CH:9]=2)=[O:5])[CH3:2]

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 23249734Ethyl 6-methoxy-1-oxo-3-phenyl-1H-indene-2-carboxylate

Produkt 1

HCID 73123866Ethyl 3-hydroxyimino-5-methoxy-1-phenylindene-2-carboxylateAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

6-Methoxy-1-oxo-3-phenyl-1H-indene-2-carboxylic acid ethyl ester (1.6 g, 5.19 mmol) obtained in Example 1 was dissolved in ethanol (100 mL), hydroxylamine hydrochloride (1.08 g, 15.57 mmol) and pyridine (1.64 g, 1.68 mL, 20.76 mmol) were added thereto, refluxed for 1 hr, and cooled to RT. The resulting mixture washed with saturated sodium bicarbonate and extracted with ethyl acetate. The organic layer was separated, dried over anhydrous MgSO4 and concentrated under a reduced pressure. The resulting residue was purified by flash chromatography to obtain 1.34 g of the titled compound (yield: 80%).

Aufarbeitung

  1. temperaturerefluxed for 1 hr
  2. washThe resulting mixture washed with saturated sodium bicarbonate
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated under a reduced pressure
  7. customThe resulting residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-dcc48670644f41dbafba0d9dcc7475a0
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745439B2

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