Reaction #2286296
ord-80bff88c65254ce1b1b9e2da6630f0cc
Reaction equation
Reactants
Reagents
Solvents
Conditions
Workup
- 1TemperatureThe reaction mixture was cooled to room temperature
- 2Concentrationconcentrated
- 3workup.ADDITIONThe resulting residue was diluted with methylene chloride (200 mL)
- 4Washwas washed with water (150 mL)
- 5OtherThe organic layer was separated
- 6workup.ADDITIONHexanes (3×200 mL) were added to the residue in portions
- 7Concentrationsubsequently concentrated under vacuum
- 8workup.ADDITIONThe resulting semi-solid was diluted with a minimum amount of ether
- 9FiltrationThe resulting white solid was filtered
- 10Washwashed with cold ether
- 11Otherdried under high vacuum overnight
Procedure
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