Hydrazine hydrate (1:1) → 6-(4-Chlorophenyl)-4,5-Dihydropyridazin-3(2H)-One

HRID 1559

Reaction equation

HRID 1559 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]([CH2:8][CH2:9][C:10](O)=[O:11])=O)=[CH:4][CH:3]=1.O.[NH2:16][NH2:17]>C(O)C>[Cl:1][C:2]1[CH:14]=[CH:13][C:5]([C:6]2[CH2:8][CH2:9][C:10](=[O:11])[NH:16][N:17]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 776043-(4-Chlorobenzoyl)propionic acid

Product 1

HCID 1209906-(4-Chlorophenyl)-4,5-Dihydropyridazin-3(2H)-OneYield 81.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-(4-chlorobenzoyl)propionic acid (20 g) in absolute ethanol (200 ml) was added 5 g of hydrazine monohydrate. A thick solid was formed which dissolved after heating. The resulting solution was refluxed for 3 h, cooled and the solid formed filtered and dried to yield 16 g (80%) of 6-(4-chlorophenyl)-4,5-dihydropyridazinone.

Workup

  1. customA thick solid was formed which
  2. dissolutiondissolved
  3. temperatureafter heating
  4. temperatureThe resulting solution was refluxed for 3 h
  5. temperaturecooled
  6. customthe solid formed
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-f026b66c93374e7dacf2ff70e1bdeab8
Source dataset
uspto-grants-1998_03
Patent number
US05726176

Linked notes

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