p-Anisohydrazide

Uses

4-Methoxybenzhydrazide is used as pharmaceutical intermediates and it is also involved in a variety of organic synthesis.

Uses

4-Methoxybenzhydrazide may be used to synthesize:

• N′-[(E)-5-bromo-2-hydroxy-3-methoxybenzylidene]-4-methoxybenzohydrazide monohydrate
• 2,5-bis(4-methoxyphenyl)-1,3,4-oxadiazole
• hydrazone ligands, which readily forms ruthenium(II) hydrazone complexes via reaction with [RuHCl(CO)(PPh₃)₃]

Synthesis Reference(s)

Journal of Medicinal Chemistry, 27, p. 1565, 1984 DOI: 10.1021/jm00378a007

Safety Profile

Poison by intravenous route. Questionable carcinogen with experimental neoplastigenic data. When heated to decomposition it emits toxic fumes of Nox.

Synthesis

4-Methoxybenzoic acid hydrazide was synthesized according to literature [22]. A mixture of methyl 4-methoxybenzoate (1.66 g, 10 mmol) with 80% hydrazine hydrate (3.6 mL, 60 mmol) in anhydrous ethanol (20 mL) was heated and refluxed for 6 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure to give a white precipitate. The crude product was recrystallized from anhydrous ethanol to give 4-methoxybenzohydrazide as colorless needle-like crystals. Yield 96%, melting point 138-139°C (literature values in accordance).

References

[1] Journal of the American Chemical Society, 2013, vol. 135, # 15, p. 5656 - 5668
[2] Journal of the Chilean Chemical Society, 2012, vol. 57, # 4, p. 1492 - 1496
[3] Spectrochimica Acta - Part A: Molecular and Biomolecular Spectroscopy, 2017, vol. 174, p. 272 - 278
[4] European Journal of Medicinal Chemistry, 1985, vol. 20, # 3, p. 257 - 266
[5] Bioorganic and Medicinal Chemistry, 2005, vol. 13, # 16, p. 4842 - 4850