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

HRID 372689

Reaction equation

HRID 372689 reaction equation
[Br: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>[Br: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 Acid2×HCID 24408BromineHCID 6891086-(4-Bromophenyl)-4,5-dihydropyridazin-3(2H)-one

Product 1

HCID 6890736-(4-Bromophenyl)-2,3-dihydropyridazin-3-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 86.3 g of 6-(p-bromophenyl)-4,5-dihydro-3(2H)-pyridazinone (prepared as described in Example 5 of U.S. Pat. No. 3,689,652) in 500 ml. of glacial acetic acid is heated to 80° C. with continuous stirring. A solution of 60 g. (19.2 ml) of bromine in 80 ml. of acetic acid is added dropwise at 75°-80° C. over a period of 1 hour. The mixture is heated with stirring on a steam bath for 1/2 hour more and then poured into 3 liters of cracked ice and water. The white solid is collected by filtration and air dried, yielding 6-(p-bromophenyl)-3(2H)-pyridazinone.

Workup

  1. customprepared
  2. temperatureThe mixture is heated
  3. filtrationThe white solid is collected by filtration and air
  4. customdried

Sources & evidence

ORD record
ord-83cb8a8b390043a18ed0dbc1f91b07a2
Source dataset
uspto-grants-1978_05
Patent number
US04092311

Linked notes

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