Reaktion #6780

Reaktionsgleichung

KOH

2-carboxy-7-methyl-4-hydroxyquinoline

PCl5

NaOH

→

2-carboxy-7-methyl-4-chloroquinoline

Ausbeute 50.0%

Lösungsmittel

POCl3

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was cooled
2. 2
   workup.ADDITIONpoured onto ice
3. 3
   FiltrationThe tan precipitate was filtered
4. 4
   FiltrationThe resultant solid was filtered
5. 5
   Sonstigedried

Vorschrift

To 20 mL POCl3 was added 2-carboxy-7-methyl-4-hydroxyquinoline (2.5 g, 12.3 mmol) and PCl5 (11.5 g, 55 mmol). The mixture was heated to 130° C. for 3 hours. The reaction mixture was cooled and poured onto ice. The solution was neutralized with solid NaOH and adjusted to pH 11 with solid KOH. The tan precipitate was filtered, slurried in 250 mL water and adjusted to pH 2 with concentrated HCl. The resultant solid was filtered and dried to afford 2-carboxy-7-methyl-4-chloroquinoline (1.34 g, 50%).

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