Hydrazine hydrate (1:1) → 6-(4-Fluorophenyl)-4,5-dihydro-3(2H)-pyridazinone

HRID 413303Notes

Reaction equation

HRID 413303 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][CH2:10][C:11]([OH:13])=O)=[CH:4][CH:3]=1.O.[NH2:16][NH2:17]>C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][CH2:10][C:11](=[O:13])[NH:16][N:17]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 1013593-(4-Fluorobenzoyl)propionic acid

Product 1

HCID 6058786-(4-Fluorophenyl)-4,5-dihydro-3(2H)-pyridazinoneYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

In a round-bottomed flask, 4-(4-fluoro-phenyl)-4-oxo-butyric acid (4.90 g, 25.0 mmol) and hydrazine hydrate (1.70 ml, 35.0 mmol) were dissolved in ethanol (50 ml), and the reaction mixture was heated to about 80° C. for about ninety minutes. The mixture was allowed to cool to room temperature and then concentrated in vacuo. The resulting solids were suspended and stirred in ethanol (10 ml) for ten minutes and the mixture was then filtered to give pure product (4.14 g, 21.5 mmol, 86% yield). LRMS ([M+H]+)=193.2; m.p. 191-193° C.

Workup

  1. temperatureto cool to room temperature
  2. concentrationconcentrated in vacuo
  3. filtrationthe mixture was then filtered

Sources & evidence

ORD record
ord-a9cbcc58b91b4de7bff44c4f7c077059
Source dataset
uspto-grants-2003_05
Patent number
US06566377B2

Reaction notes

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