Propanoyl chloride, 3-bromo- → 6-[4-(3-bromopropionamido)phenyl]-5-methyl-4,5-dihydro-3(2H)-pyridazinone

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Reaction Conditions

Reaction Steps

(-)-6-(4-Aminophenyl)-5-methyl-4,5-dihydro-3(2H)-pyridazinone (0.195 g) suspended in dichloromethane (15 ml) was cooled to 0° C. Aqueous saturated sodium bicarbonate (15 ml) was added to form a two phase system. To the organic phase was added with stirring 3-bromopropionyl chloride (0.248 g) in dichloromethane (5 ml). The mixture was allowed to warm to room temperature and vigorously stirred for 3 hours to give a fine suspension. This was filtered to give the title compound (0.279 g); [α]D25 =-333° [concentration 0.91% in dimethylformamide]: nuclear magnetic resonance spectrum consistent with racemic material. Material from another run gave C, 49.41%; H, 4.73%; H, 12.22%; Br, 23.14%: theory C, 49.72%, H, 4.77%; N, 12.43%; Br, 23.63%.

Provenance & Evidence