Benzoic acid, 4-(3-pyridinyloxy)-, hydrazide synthesis

Yield:-

Reaction Conditions:

with hydrazine in ethanol; for 24 h;Heating / reflux;

Steps:

34

Methyl 4-(pyridine-3-yloxy)benzoate (4.8 g, 20.94 mmol) was dissolved in ca. 150 mL of EtOH and anhydrous hydrazine (4.08 g, 4.0 mL) was added via a syringe. The resulting yellow solution was refluxed for 24 hrs. Then solvent was removed in vacuo to give the title product (4.8 g, 100 % yield) as yellow viscous oil, which upon standing slowly solidified.; ESI-MS: [M+H]⁺, 230, 231. ^.H NMR (DMSO-d₆): 5 4.13 (br s., 2H), 7.06-7.09 (d, J= 8.7 Hz, 2H), 7.45-7.47 (dd, J, = 8.4 Hz, J₂ = 4.9 Hz, 1H), 7.51-7.54 (dq, Jj = 8.4 Hz, J₂ = IA Hz, 1H), 7.85-7.88 (d, J= 8.8 Hz, 2H), 8.42-8.43 (m, 2H), 9.74 (s, 1H).

References:

WO2006/24034,2006,A1 Location in patent:Page/Page column 84-85