Reaktion #78162

Reaktionsgleichung

4-(4-pyridylmethyl)-1(2H)-phthalazinone

phosphorus pentoxide

triethylamine hydrochloride

3-chloro-4-fluoroaniline

sodium hydroxide

→

Title compound

1-(3-Chloro-4-fluoroanilino)-4-(4-pyridylmethyl)phthalazine

Lösungsmittel

water

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturis heated
2. 2
   Sonstigehas formed
3. 3
   workup.STIRRINGthe reaction mixture stirred for a further 3 h at 200° C
4. 4
   TemperaturAfter cooling to RT
5. 5
   Sonstigethe hyalinocrystalline reaction mixture
6. 6
   workup.STIRRINGwith intensive stirring
7. 7
   Sonstigesonication
8. 8
   WaschenThe organic phase washed with water
9. 9
   Trocknendried over sodium sulfate
10. 10
    Einengenis concentrated by evaporation
11. 11
    Sonstigethe residue recrystallized from acetate

Vorschrift

A mixture of 1.42 g (10 mmol) phosphorus pentoxide, 1.38 g (10 mmol) triethylamine hydrochloride, and 1.46 g (10 mmol) 3-chloro-4-fluoroaniline is heated and stirred in a nitrogen atmosphere at 200° C. until a homogeneous melt has formed. To the melt, 0.593 g (2.5 mmol) 4-(4-pyridylmethyl)-1(2H)-phthalazinone is added and the reaction mixture stirred for a further 3 h at 200° C. After cooling to RT, the hyalinocrystalline reaction mixture is distributed between 150 ml dichloromethane and a mixture of 10 ml water and 20 ml 2N sodium hydroxide solution with intensive stirring and sonication. The organic phase washed with water and dried over sodium sulfate is concentrated by evaporation and the residue recrystallized from acetate. Title compound is obtained after a second recrystallization from methanol/water and drying under HV (8 h at 100° C.); m.p. 185-187° C.; ESI-MS: (M+H)+=365.

Quelle