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

HRID 1906677Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]([CH3:15])[CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1.C(=O)(O)[O-].[Na+].[Br:21][CH2:22][CH2:23][C:24](Cl)=[O:25]>ClCCl>[Br:21][CH2:22][CH2:23][C:24]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]([CH3:15])[CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1)=[O:25]

Participants

Conditions

Temperature: 0 °C

Procedure

(-)-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%.

Workup

customto form a two phase system
temperatureto warm to room temperature
customto give a fine suspension
filtrationThis was filtered

Sources & evidence

ORD record: ord-0df2e25cfe0741bf8cbe15ea8c2add70
Source dataset: uspto-grants-1987_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04652563

Reaction notes

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