反応 #78162

反応方程式

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

溶媒

water

dichloromethane

反応条件

後処理

1. 1
   温度is heated
2. 2
   その他has formed
3. 3
   workup.STIRRINGthe reaction mixture stirred for a further 3 h at 200° C
4. 4
   温度After cooling to RT
5. 5
   その他the hyalinocrystalline reaction mixture
6. 6
   workup.STIRRINGwith intensive stirring
7. 7
   その他sonication
8. 8
   洗浄The organic phase washed with water
9. 9
   乾燥dried over sodium sulfate
10. 10
    濃縮is concentrated by evaporation
11. 11
    その他the residue recrystallized from acetate

実験手順

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.

出典