反応 #78138

反応方程式

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

phosphorus pentoxide

triethylamine hydrochloride

4-chloroaniline

ammonia

→

title compound

1-(4-Chloroanilino)-4-(4-pyridylmethyl)phthalazine

溶媒

water

chloroform

反応条件

後処理

1. 1
   温度is heated
2. 2
   その他has formed (about 20 min)
3. 3
   workup.STIRRINGthe reaction mixture is stirred for 3 h at 200° C
4. 4
   温度After the reaction mixture has cooled to about 100° C.
5. 5
   workup.STIRRINGStirring
6. 6
   その他reaches about 30° C.
7. 7
   その他As soon as a diphasic mixture has formed
8. 8
   その他the organic phase is separated off
9. 9
   乾燥dried over anhydrous sodium sulfate
10. 10
    ろ過filtered
11. 11
    その他the filtrate evaporated on a RE to a volume of about 50 ml
12. 12
    workup.ADDITIONto which 100 ml acetate is then added
13. 13
    温度the mixture is cooled in an ice bath
14. 14
    その他The crystallizate obtained
15. 15
    ろ過is filtered off
16. 16
    洗浄washed with acetate and ether
17. 17
    その他After recrystallization from methanol
18. 18
    その他drying under HV for 8 h at 120° C.

実験手順

A mixture of 14.19 g (0.1 mol) phosphorus pentoxide, 13.77 g (0.1 mol) triethylamine hydrochloride and 12.76 g (0.1 mol) 4-chloroaniline is heated and stirred in a nitrogen atmosphere at 200° C. until a homogeneous melt has formed (about 20 min). To the melt, 5.93 g (0.025 mol) 4-(4-pyridylmethyl)-1(2H)-phthalazinone (for preparation see German Auslegeschrift no. 1061 788 [published Jul. 23, 1959]) is added, and the reaction mixture is stirred for 3 h at 200° C. After the reaction mixture has cooled to about 100° C., 200 ml of water is added. Stirring is continued until the temperature reaches about 30° C., and then 20 ml conc. ammonia (30% aqueous ammonium hydroxide solution) and 900 ml chloroform are added consecutively. As soon as a diphasic mixture has formed, the organic phase is separated off, dried over anhydrous sodium sulfate, filtered, and the filtrate evaporated on a RE to a volume of about 50 ml, to which 100 ml acetate is then added, and the mixture is cooled in an ice bath. The crystallizate obtained is filtered off and washed with acetate and ether. After recrystallization from methanol and drying under HV for 8 h at 120° C., the title compound is obtained; m.p. 194-195° C.; ESI-MS: (M+H)+=347.

出典