Acetic Acid → 6-(4-Chlorophenyl)-2,3-dihydropyridazin-3-one

HRID 1498

Reaction equation

HRID 1498 reaction equation
[Cl: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.C(O)(=O)C.BrBr>O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24408BromineHCID 1209906-(4-Chlorophenyl)-4,5-Dihydropyridazin-3(2H)-One

Product 1

HCID 6890856-(4-Chlorophenyl)-2,3-dihydropyridazin-3-oneYield 93.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 6-(4-chlorophenyl)-4,5-dihydropyridazinone (11.75 g) and glacial acetic acid (100 ml) was added dropwise 3 ml of bromine and the mixture was heated at 60°-70° C. for 3 h. The resulting mixture was cooled and slowly poured into 400 ml of cold water. The resulting white solid was filtered and dried to yield 10.83 g (89%) of 6-(4-chlorophenyl)pyridazinone.

Workup

  1. temperaturethe mixture was heated at 60°-70° C. for 3 h
  2. temperatureThe resulting mixture was cooled
  3. filtrationThe resulting white solid was filtered
  4. customdried

Sources & evidence

ORD record
ord-3ad3598473f04955b043e8d47bb746e6
Source dataset
uspto-grants-1998_03
Patent number
US05726162

Linked notes

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