반응 #56672

반응 방정식

4-Acetylbenzoic acid

glyoxalic acid monohydrate

Methyl hydrazine

→

4-(1-methyl-6-oxo-1,6-dihydro-pyridazin-3-yl)-benzoic acid

용매

acetic acid

반응 조건

후처리

1. 1
   기타Solvent was removed with evaporator in vacuo
2. 2
   workup.ADDITIONTo the residue was added water (15 mL)
3. 3
   온도the mixture cooled with an ice bath
4. 4
   온도the mixture was heated
5. 5
   온도to reflux for 5 hours
6. 6
   농축The solution was concentrated in vacuo
7. 7
   workup.ADDITIONTo the solid residue was added 1 M cold aqueous hydrochloric acid until the solution
8. 8
   여과The solid was filtrated
9. 9
   기타dried in vacuo over night
10. 10
    workup.ADDITIONThe solids were treated with diethyl ether (200 mL)
11. 11
    기타the mixture was ultrasonicated at room temperature for 3 hours
12. 12
    여과filtered
13. 13
    workup.ADDITIONThe solids were treated with 200 mL of diethyl ether
14. 14
    기타after drying

실험 절차

4-Acetylbenzoic acid (5.00 gram, 30.5 mmol) and 3.19 gram of glyoxalic acid monohydrate (34.7 mmol, 1.14 eq.) were stirred in 50 mL of acetic acid at 110° C. for 20 hours, and then cooled to 40° C. Solvent was removed with evaporator in vacuo. To the residue was added water (15 mL), and the mixture cooled with an ice bath. The resulting solution was titrated with ammonia solution until pH 9. Methyl hydrazine (3.00 mL 57.3 mmol, 1.88 eq.) was added, and the mixture was heated to reflux for 5 hours. The solution was concentrated in vacuo. To the solid residue was added 1 M cold aqueous hydrochloric acid until the solution had a pH 1˜2. The solid was filtrated and dried in vacuo over night. The solids were treated with diethyl ether (200 mL) and the mixture was ultrasonicated at room temperature for 3 hours and filtered. The solids were treated with 200 mL of diethyl ether and stirred for 2 hours before filtration, which after drying gave 4-(1-methyl-6-oxo-1,6-dihydro-pyridazin-3-yl)-benzoic acid in 33% isolated yield.

출처