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Acetic Acid → HCID 59354866, Verbindung

HRID 1425895
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1425895
[CH3:1][C:2]1([CH3:35])[C:6](=[O:7])[C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]3[CH:25]=[CH:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[N:17]=3)=[CH:10][CH:9]=2)=[C:4]([C:26]2[CH:31]=[CH:30][C:29]([N+:32]([O-])=O)=[CH:28][CH:27]=2)[O:3]1.CC(O)=O>C(O)C.[Fe]>[NH2:32][C:29]1[CH:30]=[CH:31][C:26]([C:4]2[O:3][C:2]([CH3:1])([CH3:35])[C:6](=[O:7])[C:5]=2[C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]3[CH:25]=[CH:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[N:17]=3)=[CH:10][CH:9]=2)=[CH:27][CH:28]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 176Acetic AcidHCID 593548082,2-dimethyl-5-(4-nitrophenyl)-4-(4-(quinolin-2-ylmethoxy)phenyl)furan-3(2H)-one

Produkt 1

HCID 59354866HCID 59354866, VerbindungAusbeute 71,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

To a stirred solution of 2,2-dimethyl-5-(4-nitrophenyl)-4-(4-(quinolin-2-ylmethoxy)phenyl)furan-3(2H)-one (0.6 g, 1.28 mmol) in ethanol (10 mL) was added AcOH (1.28 mL) at RT under N2 atmosphere. After being stirred for 10 min at RT, the reaction mixture was heated to 70° C. and Fe (0.524 g, 9.04 mmol) and FeCl3 (0.062 g, 0.38 mmol) were added under N2 atmosphere. The reaction mixture was stirred at 70° C. for 2 h. After completion of starting material (by TLC), reaction mixture was cooled to RT, and the volatiles were evaporated in vacuo to obtain the crude product. The crude product was extracted in EtOAc (25 mL), washed with water (2×10 mL), brine and dried over anhydrous Na2SO4. After filtration and evaporation, the crude material was purified by silica gel column chromatography to afford 5-(4-aminophenyl)-2,2-dimethyl-4-(4-(quinolin-2-ylmethoxy)phenyl) furan-3(2H)-one (400 mg, 71%), as a yellow solid.

Aufarbeitung

  1. temperaturethe reaction mixture was heated to 70° C.
  2. stirringThe reaction mixture was stirred at 70° C. for 2 h
  3. customAfter completion of starting material (by TLC), reaction mixture
  4. temperaturewas cooled to RT
  5. customthe volatiles were evaporated in vacuo
  6. customto obtain the crude product
  7. extractionThe crude product was extracted in EtOAc (25 mL)
  8. washwashed with water (2×10 mL), brine
  9. dry with materialdried over anhydrous Na2SO4
  10. filtrationAfter filtration and evaporation
  11. customthe crude material was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f75db0e8b9dc4c15b79220b55a3eebdd
Quelldatensatz
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08933074B2

Notizen zur Reaktion

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