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

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

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P405Store locked up.

P501Dispose of contents/container to..…

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

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