Potassium Hydroxide → 1-amino-4-hydroxyquinolin-2(1H)-one

HRID 552095Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 552095
[OH-].[K+].[OH:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]([N:14]=CC2C=CC=CC=2)[C:6](=[O:22])[C:5]=1C(OCC)=O>O1CCOCC1>[NH2:14][N:7]1[C:8]2[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:4]([OH:3])=[CH:5][C:6]1=[O:22]

Komponenten

4

Edukt 2

HCID 14797Potassium HydroxideHCID 67063863Ethyl 4-hydroxy-2-oxo-1-{[phenylmethylene]amino}-1,2-dihydroquinoline-3-carboxylate

Produkt 1

HCID 591688071-amino-4-hydroxyquinolin-2(1H)-oneAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of 25% by weight aqueous potassium hydroxide (200 mL) and 1,4-dioxane (50 mL) heated to 90-100° C. was added portion wise ethyl 4-hydroxy-2-oxo-1-{[phenylmethylene]amino}-1,2-dihydroquinoline-3-carboxylate (6.72 g, 20.0 mmol). The reaction mixture was heated at reflux for 90 minutes allowing distillation to occur and additional water and dioxane (30 mL each) were added to the reaction vessel to reach the original volume. The mixture was refluxed for an additional 90 minutes with distillation, cooled, washed with 200 mL of 1:1 diethyl ether/ethyl acetate, acidified with concentrated hydrochloric acid to pH 2 and the resulting solid was collected by filtration, washed with water and dried to constant mass to give 1-amino-4-hydroxyquinolin-2(1H)-one as a tan sold (3.22 g, 91% yield). MS (DCI) m/z 177 (M+H)+. 1H NMR (300 MHz, DMSO-d6) δ 5.56 (s, 2 H) 5.94 (s, 1 H) 7.20 (t, J=7.54 Hz, 1 H) 7.62 (m, 1 H) 7.85 (m, 2 H) 11.33 (s, 1 H).

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 90 minutes
  3. distillationdistillation
  4. additionadditional water and dioxane (30 mL each) were added to the reaction vessel
  5. temperatureThe mixture was refluxed for an additional 90 minutes with distillation
  6. temperaturecooled
  7. washwashed with 200 mL of 1:1 diethyl ether/ethyl acetate
  8. filtrationthe resulting solid was collected by filtration
  9. washwashed with water
  10. customdried to constant mass

Quellen und Nachweise

ORD-Eintrag
ord-78a13afd68c243248e0ee2c3512cbedf
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07951800B2

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