Reaction #8089

Reaction equation

sodium hydrogencarbonate

4-methoxycarbonyl-6-[4-(methylthio)-phenyl]-2H-pyridazin-3-one

potassium carbonate

isobutyl bromide

→

title compound

Yield 65.1%

4-carboxy-2-isobutyl-6-[4-(methylthio)-phenyl]-2H-pyridazin-3-one

Yield 65.1%

Solvents

N,N-dimethylformamide

Conditions

Workup

1. 1
   Otherto drop back to room temperature
2. 2
   ExtractionThe mixture was then extracted with ethyl acetate
3. 3
   WashThe extract was washed with brine
4. 4
   Dryingdried over anhydrous sodium sulfate
5. 5
   workup.DISTILLATIONThe solvent was distilled off
6. 6
   Otherthe residue was reacted

Procedure

To a solution of 4-methoxycarbonyl-6-[4-(methylthio)-phenyl]-2H-pyridazin-3-one (8.00 g, 29.0 mmol) in N,N-dimethylformamide (80 mL) were added potassium carbonate (8.02 g, 58.0 mmol) and isobutyl bromide (4.76 g, 34.8 mmol), and the mixture was stirred at 80° C. for 2 hours. The temperature of the reaction mixture was allowed to drop back to room temperature, and a saturated aqueous solution of sodium hydrogencarbonate was added. The mixture was then extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous sodium sulfate. The solvent was distilled off. Following the procedure of Example 1 (7), the residue was reacted to yield the title compound as a yellow solid [yield: 65.1% (2 steps)].

Source