Reaktion #348145

Reaktionsgleichung

(4-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)-5-fluoro-2-nitrophenoxy)-acetic acid, ethyl ester

→

6-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)-7-fluoro-2H-1,4-benzoxazin-3-(4H)-one

Ausbeute 80.0%

Lösungsmittel

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe heat
2. 2
   Sonstigenitrogen were removed
3. 3
   TemperaturThe solution was cooled
4. 4
   Filtrationfiltered through Celite®
5. 5
   workup.ADDITIONThe filtrate was diluted with 100 mL water
6. 6
   Extraktionextracted three times with ethyl acetate
7. 7
   WaschenThe ethyl acetate extracts were washed with a saturated NaHCO3 solution
8. 8
   Trocknendried over anhydrous MgSO4
9. 9
   Einengenconcentrated in vacuo
10. 10
    SonstigeThe residue was recrystallized from methylcyclohexane/ethyl acetate

Vorschrift

A solution of 4.5 g (0.0106 mole) (4-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)-5-fluoro-2-nitrophenoxy)-acetic acid, ethyl ester in 75 mL acetic acid was heated to 80° C. under a nitrogen atmosphere. The heat and nitrogen were removed and 1.8 g (0.033 mole) iron powder was added in 3 portions over 5 min. The solution was stirred at 80° C. for an additional 3 hours. The solution was cooled and filtered through Celite®. The filtrate was diluted with 100 mL water and extracted three times with ethyl acetate. The ethyl acetate extracts were washed with a saturated NaHCO3 solution, dried over anhydrous MgSO4, and concentrated in vacuo. The residue was recrystallized from methylcyclohexane/ethyl acetate to give 2.95 g (80%) of 6-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)-7-fluoro-2H-1,4-benzoxazin-3-(4H)-one as a white solid, mp 207° C.

Quelle