Reaktion #82691

Reaktionsgleichung

2,4-dihydroxyquinoline

HNO3

water

→

title compound

Ausbeute 83.0%

3-Nitro4-hydroxy-1,2-dihydroquinolin-2-one

Ausbeute 83.0%

Lösungsmittel

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was cooled to room temperature
2. 2
   FiltrationThe mixture was filtered
3. 3
   Waschenwashed with water
4. 4
   Sonstigedried

Vorschrift

To a mixture of 1.45 g (9.00 mmol) of 2,4-dihydroxyquinoline (Aldrich) in 10 mL of glacial acetic acid was added 2.5 mL of HNO3 (69-71%). The mixture was heated at 90° C. for 5 min to become a red solution, then a precipitate was observed in the solution. The mixture was cooled to room temperature, then was added 40 mL of water and the mixture was stirred for 20 min. The mixture was filtered and washed with water, dried to leave 1.54 g (83%) of title compound as a yellow solid, mp 216° C. (decomposed, lit: Buckle, D. R., et al., J. Med. Chem. 18:726-732 (1975), 216° C.). 1H NMR (CDCl3 +DMSO-d6), 7.013 (t, 1, J=7.5), 7.105 (d, 1, J=7.5), 7.396 (t, 1, J=7.2), 7.877 (d, 1, 7.8), 11.72 (mb 1).

Quelle