6-[2-(tert-Butoxycarbonyl)hydrazinyl]nicotinic acid Chemical Properties

Melting point:

126 °C

Density 

1.312

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

2.61±0.10(Predicted)

form 

Solid

color 

White to Off-White

6-[2-(tert-Butoxycarbonyl)hydrazinyl]nicotinic acid Usage And Synthesis

Uses

6-[2-(tert-Butoxycarbonyl)hydrazinyl]nicotinic acid is used as a pharmaceutical intermediate in pharmaceutical synthesis and scientific research.

Synthesis

Di-tert-butyl dicarbonate (0.40 g, 1.82 mmol) was added to an N,N-dimethylformamide (DMF) solution of 6-hydrazinylpyridine-3-carboxylic acid (0.346 g, 1.82 mmol) and triethylamine (0.32 mL, 2.36 mmol). The reaction mixture was stirred at 25 °C for 1 h to become homogeneous, and stirring was continued for 16 h. The reaction was carried out under reduced pressure. After completion of the reaction, the solvent was removed under reduced pressure. The residue was diluted with a solvent mixture of ethyl acetate/methanol (4:1, v/v) and purified by silica gel column chromatography, using ethyl acetate as eluent, to afford 6-[2-(tert-butoxycarbonyl)hydrazinyl]nicotinic acid (4b) as a light yellow solid (0.44 g, 96% yield).IR (ATR, cm-1): 3353, 3227, 2975, 1719, 1593, 1472, 1372, 1256, 1014, 867, 794, 520. 1H NMR (DMSO-d6, δ): 12.584 (s, 1H), 8.59 (s, 1H), 7.97 (d, J = 9 Hz, 1H), 6.54 (d, J = 9 Hz, 1H). 13C NMR (DMSO-d6, δ): 166.6 , 155.7, 150.5, 138.5, 116.7, 79.3, 28.1, 14.0. MS (ESI-): [M-H]- m/z 252.00. MS (ESI+): [M+H]+ m/z 254.07. HRMS (ESI+): [M+H]+ m/z 254.1145 (calculated values) C11H16N3O4, 254.1141).

References

[1] Letters in Organic Chemistry, 2014, vol. 11, # 3, p. 208 - 214
[2] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 16, p. 4764 - 4767
[3] Polish Journal of Chemistry, 2004, vol. 78, # 7, p. 951 - 959
[4] Journal of Labelled Compounds and Radiopharmaceuticals, 2018, vol. 61, # 2, p. 68 - 76
[5] Pharmazie, 2006, vol. 61, # 4, p. 269 - 273

6-[2-(tert-Butoxycarbonyl)hydrazinyl]nicotinic acid(133081-25-1)Related Product Information

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