Hydrazine hydrate (1:1) → 6-(4-Bromophenyl)-4,5-dihydropyridazin-3(2H)-one

HRID 970009

Reaction equation

HRID 970009 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].O>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 24654Hydrazine hydrate (1:1)HCID 806463-(4-Bromobenzoyl)propionic acid

Product 1

HCID 6891086-(4-Bromophenyl)-4,5-dihydropyridazin-3(2H)-oneYield 98.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-(4-Bromo-phenyl)-4-oxo-butyric acid (Aldrich, 25.0 g, 97.3 mmol) was treated with NH2NH2—H2O (Aldrich, 55%, 9.1 mL, 156 mmol) in EtOH (Aldrich, 100 mL) at refluxing for 2 h. It was cooled down to ambient temperature and the white solid was filtered off to give the title compound (24.2 g, 98%). 1H NMR (CDCl3, 300 MHz) δ 2.50-2.76 (m, 2H), 2.85-3.09 (m, 2H), 7.43-7.71 (m, 4H), 8.55 (s, 1H) ppm. MS (DCl/NH3) m/z 253 (M+H)+, 255 (M+H)+, 270 (M+NH4)+, 272 (M+NH4)+.

Workup

  1. temperatureat refluxing for 2 h
  2. filtrationthe white solid was filtered off

Sources & evidence

ORD record
ord-f40bd48d7f084095af3e1c39053a635a
Source dataset
uspto-grants-2007_12
Patent number
US07309699B2

Linked notes

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