Reacción #2286296

Ecuación de reacción

sodium acetate

[3,5-dichloro-4-(6-chloro-5-isopropyl-pyridazin-3-yloxy)-phenyl]-acetic acid

[3,5-Dichloro-4-(6-chloro-5-isopropyl-pyridazin-3-yloxy)-phenyl]-acetic acid

→

[3,5-dichloro-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-acetic acid

Rendimiento 65.0%

[3,5-Dichloro-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-acetic acid

Rendimiento 65.0%

Disolventes

acetic acid

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction mixture was cooled to room temperature
2. 2
   Concentraciónconcentrated
3. 3
   workup.ADDITIONThe resulting residue was diluted with methylene chloride (200 mL)
4. 4
   Lavadowas washed with water (150 mL)
5. 5
   OtroThe organic layer was separated
6. 6
   workup.ADDITIONHexanes (3×200 mL) were added to the residue in portions
7. 7
   Concentraciónsubsequently concentrated under vacuum
8. 8
   workup.ADDITIONThe resulting semi-solid was diluted with a minimum amount of ether
9. 9
   FiltraciónThe resulting white solid was filtered
10. 10
    Lavadowashed with cold ether
11. 11
    Otrodried under high vacuum overnight

Procedimiento

A mixture of glacial acetic acid (200 mL), sodium acetate (6.1 g, 74.4 mmol) and [3,5-dichloro-4-(6-chloro-5-isopropyl-pyridazin-3-yloxy)-phenyl]-acetic acid (18) (8.3 g, 21.96 mmol) was heated to 125° C. for 24 h. The reaction mixture was cooled to room temperature and concentrated. The resulting residue was diluted with methylene chloride (200 mL) and was washed with water (150 mL). The organic layer was separated. Hexanes (3×200 mL) were added to the residue in portions and then subsequently concentrated under vacuum. The resulting semi-solid was diluted with a minimum amount of ether, scratched, and slurried. The resulting white solid was filtered, washed with cold ether and dried under high vacuum overnight to afford [3,5-dichloro-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-acetic acid (19) (5.1 g, 65%) as a white solid; LRMS for C15H14Cl2N2O4 (M+) m/z=357. Molecular Weight=357.1958; Exact Mass=356.0331

Fuente