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

HRID 1906662Notes

Reaction equation

HRID 1906662 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

HCID 84944Propanoyl chloride, 3-bromo-HCID 161928Ici 109,081

Product 1

HCID 140033506-[4-(3-bromopropionamido)phenyl]-5-methyl-4,5-dihydro-3(2H)-pyridazinoneYield 97%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

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.

Workup

  1. temperatureunder reflux for 16 hours
  2. temperatureto cool
  3. customthe solid product collected
  4. customdried
  5. stirringstirred with water (500 ml) for 30 minutes
  6. customThe crude product was collected
  7. washwashed with water (500 ml)
  8. customdried

Sources & evidence

ORD record
ord-63e8f65e5bda48dc9fd97eb19fbad592
Source dataset
uspto-grants-1987_03
Patent number
US04652563

Reaction notes

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