Sodium Hydroxide → 7-Hydroxy-1.2,3,4-tetrahydro-4-quinolinone

HRID 1859818Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1859818
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7](=[O:13])[CH2:8][CH2:9][NH:10]2)=[CH:5][CH:4]=1.B(Br)(Br)Br.[OH-].[Na+]>C(Cl)Cl>[OH:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7](=[O:13])[CH2:8][CH2:9][NH:10]2)=[CH:5][CH:4]=1

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 46408157-Methoxy-1,2,3,4-tetrahydroquinolin-4-one

Produkt 1

HCID 186264847-Hydroxy-1.2,3,4-tetrahydro-4-quinolinoneAusbeute 49,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A solution of 1.1 g (6.2 mmol) of 7-methoxy-1,2,3,4-tetrahydro-4-quinolinone (Rec. Trav. Chim., 1963;82:39) in 35 mL of CH2Cl2 was cooled in ice and treated with 5.0 mL of BBr3. After stirring at 0° C. for 0.5 hour, the solution was allowed to stir at room temperature overnight. The solution was poured into ice water and made basic with 50% NaOH. After extracting with Et2O, the pH was brought to 5.5 with dilute HCl, and the solution extracted twice with EtOAc. The EtOAc was washed with saturated NaCl and dried over MgSO4. Removal of the solvent under reduced pressure gave 0.5 g (49.5% yield) of the product as an orange solid. The structure was confirmed by NMR and mass spectroscopy. MS m/z 164 (M+H+).

Aufarbeitung

  1. stirringto stir at room temperature overnight
  2. extractionAfter extracting with Et2O
  3. extractionthe solution extracted twice with EtOAc
  4. washThe EtOAc was washed with saturated NaCl
  5. dry with materialdried over MgSO4
  6. customRemoval of the solvent under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-059bf9ba81eb47dabcbbfdda555a7c55
Quelldatensatz
uspto-grants-2003_03
Patentnummer
US06528535B2

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