pyridine-2-carboximidohydrazide Chemical Properties

Melting point:

95-96 °C

Boiling point:

262.4±32.0 °C(Predicted)

Density 

1.31±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,Store in freezer, under -20°C

pka

7.38±0.50(Predicted)

Appearance

Yellow to orange Solid

EPA Substance Registry System

2-Pyridinecarboximidic acid, hydrazide (1005-02-3)

Safety Information

TSCA 

TSCA listed

pyridine-2-carboximidohydrazide Usage And Synthesis

Synthesis

General procedure for the synthesis of 3-(2-pyridyl)aminohydrazone from 2-cyanopyridine: In a 1 L four-necked round-bottomed flask equipped with a mechanical stirrer, a reflux condenser, and a nitrogen inlet/outlet, 2-pyridinecarbonitrile (50 g, 480 mmol), hydrazine hydrate (26.4 g, 528 mmol), and ethanol (25 mL) were added. The resulting mixture was stirred at room temperature for 6 h. Subsequent detection by TLC showed that some of the starting material remained unreacted. 7.2 g (144 mmol) of hydrazine hydrate was added and the mixture was heated at 50 °C for 3 hours. After completion of the reaction, the mixture was cooled in an ice bath, filtered and dried to give 40.2 g of solid product. The mother liquor was concentrated, ground with hexane and dried to give another 11.6 g of solid product (total 51.8 g, 381 mmol, 79% yield). The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3): δ 8.50 (m, 1H, Ar-H), 8.01 (d, 1H, Ar-H), 7.68 (t, 1H, Ar-H), 7.28 (m, 1H, Ar-H), 5.38 (br s, 2H, -NH2), 4.62 (br s, 1H, -NH). 2.40 (br s, 1H, -NH).

References

[1] Patent: US2016/244860, 2016, A1. Location in patent: Paragraph 0168-0169
[2] Molecular Crystals and Liquid Crystals, 2010, vol. 520, p. 68 - 74
[3] Molecular Crystals and Liquid Crystals, 2012, vol. 567, # 1, p. 156 - 162,7
[4] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 14, p. 3287 - 3290
[5] Inorganic Chemistry, 2017, vol. 56, # 24, p. 15259 - 15270