Hydrazine → 6-(4-Bromophenyl)-4,5-dihydropyridazin-3(2H)-one

HRID 747922

Reaction equation

HRID 747922 reaction equation
[Br: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.[NH2:15][NH2:16]>CCO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][CH2:10][C:11](=[O:13])[NH:15][N:16]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 806463-(4-Bromobenzoyl)propionic acid

Product 1

HCID 6891086-(4-Bromophenyl)-4,5-dihydropyridazin-3(2H)-oneYield 97.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-(4-bromo-phenyl)-4-oxo-butyric acid (Aldrich, 25.0 g, 97.3 mmol) in EtOH (100 mL) was treated with aqueous hydrazine (Aldrich, 55%, 9.1 mL, 100 mmol) at 80° C. for 2 h. The mixture was cooled to room temperature and the precipitate was collected by filtration and dried under vacuum to provide the title compound (24 g, 97% yield). 1H NMR (300 MHz, CDCl3) δ 2.35-2.76 (m, 2H), 2.80-3.11 (m, 2H), 7.45-7.77 (m, 4H), 8.55 (s, 1H); MS (DCl/NH3) m/z 253 (M+H)+, 255 (M+H)+.

Workup

  1. filtrationthe precipitate was collected by filtration
  2. customdried under vacuum

Sources & evidence

ORD record
ord-179af31ea9424805b45fd221ba40b273
Source dataset
uspto-grants-2008_07
Patent number
US07399765B2

Linked notes

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