3-Chloropropionyl chloride → 6-[p-(3-chloropropionylamino)-phenyl]-4,5-dihydro-3(2H)-pyridazinone

HRID 354679Notes

Reaction equation

HRID 354679 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1.[Cl:15][CH2:16][CH2:17][C:18](Cl)=[O:19]>C1C=CC=CC=1>[Cl:15][CH2:16][CH2:17][C:18]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1)=[O:19]

Participants

4

Reactant 2

HCID 693643-Chloropropionyl chlorideHCID 6767506-(4-Aminophenyl)-4,5-dihydropyridazin-3(2H)-one

Product 1

HCID 133851966-[p-(3-chloropropionylamino)-phenyl]-4,5-dihydro-3(2H)-pyridazinoneYield 97.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

18.9 g (0.10 mole) of 6-(p-aminophenyl)-4,5-dihydropyridaz-3-one and 15.2 g (0.12 mole) of 3-chloropropionyl chloride in 90 ml of absolute benzene are refluxed for 2 hours. The product is filtered off at 10° C., washed first with benzene and then with water, and dried under reduced pressure at 100° C. 27.2 g (97% of theory) of 6-[p-(3-chloropropionylamino)-phenyl]-4,5-dihydropyridaz-3-one are obtained as a colorless substance which, after recrystallization from dimethylformamide/water, melts, with decomposition, at 226°-227° C.

Workup

  1. filtrationThe product is filtered off at 10° C.
  2. washwashed first with benzene
  3. dry with materialwith water, and dried under reduced pressure at 100° C

Sources & evidence

ORD record
ord-289e84e5104340909aa7433fc67501cc
Source dataset
uspto-grants-1983_03
Patent number
US04376771

Reaction notes

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