Propanoyl chloride, 3-bromo- → 6-[4-(3-bromopropionamido)phenyl]-5-methyl-4,5-dihydro-3(2H)-pyridazinone
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.[Br:16][CH2:17][CH2:18][C:19](Cl)=[O:20]>C1(C)C=CC=CC=1>[Br:16][CH2:17][CH2:18][C:19]([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:20]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A suspension of 6-(4-aminophenyl)-5-methyl-4,5-dihydro-3(2H)-pyridazinone (Curran et al., J. Med. Chem. 17, 273 (1974)) (75.0 g, 0.369 mol) and 3-bromoproionylchloride (100 g, 0.583 mol) in toluene (800 ml) was stirred under reflux for 16 hours. The reaction mixture was allowed to cool and the solid product collected, dried and stirred with water (500 ml) for 30 minutes. The crude product was collected, washed with water (500 ml) and dried to give 6-[4-(3-bromopropionamido)phenyl]-5-methyl-4,5-dihydro-3(2H)-pyridazinone (120 g, 97%), m.p. 215°-217° C.