Reaktion #442867

Reaktionsgleichung

2-amino-3-nitrophenol

2-fluorobenzoyl chloride

→

2-fluoro-N-(2-hydroxy-6-nitrophenyl)benzamide

Ausbeute 85.1%

Lösungsmittel

pyridine

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter heating
2. 2
   Temperaturunder reflux for 4 hours
3. 3
   Einengenthe mixture was concentrated
4. 4
   workup.ADDITIONThen dilute hydrochloric acid and ethyl acetate were added
5. 5
   SonstigeThe organic layer was separated
6. 6
   Waschenwashed with water
7. 7
   EinengenAfter concentrating
8. 8
   workup.ADDITION20 ml of tetrahydrofuran and 20 ml of 1N sodium hydroxide were added
9. 9
   Temperaturthe mixture was heated
10. 10
    Temperaturunder reflux for 4 hours
11. 11
    TemperaturAfter cooling
12. 12
    Einengenconcentrated
13. 13
    workup.ADDITIONAfter adding ethyl acetate and water
14. 14
    Sonstigethe organic layer was separated
15. 15
    Waschenwashed with water
16. 16
    Trocknendried over magnesium sulfate
17. 17
    EinengenAfter concentrating
18. 18
    Sonstigethe residue was purified by silica gel column chromatography

Vorschrift

1.57 g (10 mmol) of 2-amino-3-nitrophenol was dissolved in 20 ml of pyridine and 3.36 g (21 mmol) of 2-fluorobenzoyl chloride was added thereto under stirring. After heating under reflux for 4 hours, the mixture was concentrated. Then dilute hydrochloric acid and ethyl acetate were added thereto. The organic layer was separated and washed with water. After concentrating, 20 ml of tetrahydrofuran and 20 ml of 1N sodium hydroxide were added and the mixture was heated under reflux for 4 hours. After cooling, it was neutralized with hydrochloric acid and concentrated. After adding ethyl acetate and water, the organic layer was separated, washed with water and dried over magnesium sulfate. After concentrating, the residue was purified by silica gel column chromatography. Thus 2.35 g of 2-fluoro-N-(2-hydroxy-6-nitrophenyl)benzamide was obtained. 553 mg (2 mmol) of this powder was dissolved in 20 ml of dimethylformamide and 332 mg (2.4 mmol) of potassium carbonate and 20 mg of a copper powder were added thereto. After heating under reflux for 3 hours and concentrating, ethyl acetate and dilute hydrochloric acid were added to the residue. The formed insoluble matters were filtered off and the organic layer was separated, washed with water, dried over magnesium sulfate and concentrated. Then the residue was purified by silica gel column chromatography. Thus 400 mg of the title compound was obtained.

Quelle