Hydrochloric Acid → 4-[5-(4-Chlorophenyl)-2-ethylphenyl]-5-methoxy-2,6-dimethyl-2,3-dihydro-3-pyridazinone

Participants

Reaction Conditions

Reaction Steps

To a 25 ml volume three-necked flask, 1-[2-[5-(4-chlorophenyl)-2-ethylphenyl]-2-oxoacetyl]-1-methyl-2-(1-methylsulfonyl-2-propylidene)hydrazine ((4-34)-(1)-67) (853 mg), toluene (1.76 ml), and methanol (1.85 ml) were added under a nitrogen atmosphere, then added lithium hydroxide monohydrate (83 mg) at 0° C. After the mixture was stirred at 0° C. for 3 hours, 10 w/w % of hydrochloric acid was added to adjust pH to less than 1, and extracted with toluene 3 times. The organic layers were combined, and concentrated under reduced pressure. The residue was subjected to column chromatography (hexane: ethyl acetate=3:1) to give 349 mg of 4-[5-(4-chlorophenyl)-2-ethylphenyl]-2,6-dimethyl-5-methylsulfonyl-2,3-dihydro-3-pyridazinone ((2-34)-(1)-67) and 66 mg of 4-[5-(4-chlorophenyl)-2-ethylphenyl]-5-methoxy-2,6-dimethyl-2,3-dihydro-3-pyridazinone (31-a).

Provenance & Evidence