Sulfuric Acid → 4-(2,6-Diethyl-4-methylphenyl)-5-methoxy-2,6-dimethyl-2,3-dihydro-3-pyridazinone

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Reaction Conditions

Reaction Steps

To a 25 mL volume three-necked flask, 1-[2-(2,6-diethyl-4-methylphenyl)-2-oxoacetyl]-1-methyl-2-(1-methylsulfonyl-2-propylidene)hydrazine ((4-34)-(1)-39) (1.00 g) and methanol (3.8 ml) were added under a nitrogen atmosphere, and cooled to 0° C. To the mixture was added toluene (1.15 g) and lithium hydroxide monohydrate (56 mg). After the mixture was stirred at 0° C. for 4 hours and at 5 for 16 hours, 48 w/w % of aqueous sodium hydroxide solution (445 mg) was added at 5° C., and stirred at room temperature for 1.5 hours and at 60° C. for 3 hours. To the mixture, water and toluene were added, then 20 w/w % of sulfuric acid was added to adjust pH to less than 1. After the organic layer was removed, the aqueous layer was extracted with toluene 2 times. The organic layers were combined, washed with saturated brine, and concentrated under reduced pressure to give 746 mg of 4-(2,6-diethyl-4-methylphenyl)-5-methoxy-2,6-dimethyl-2,3-dihydro-3-pyridazinone (31-b).

Provenance & Evidence