N-(2-HYDROXYETHYL)NITOTINAMIDE Chemical Properties

Melting point:

92 °C

Boiling point:

185-195 °C(Press: 0.4-0.6 Torr)

Density 

1.212±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly), Water (Slightly)

form 

Solid

pka

12.94±0.46(Predicted)

color 

White to Pale Yellow

InChI

InChI=1S/C8H10N2O2/c11-5-4-10-8(12)7-2-1-3-9-6-7/h1-3,6,11H,4-5H2,(H,10,12)

InChIKey

SJZLOWYUGKIWAK-UHFFFAOYSA-N

SMILES

C1=NC=CC=C1C(NCCO)=O

N-(2-HYDROXYETHYL)NITOTINAMIDE Usage And Synthesis

Uses

N-(2-Hydroxyethyl)nitotinamide is an intermediate used to prepare oxadiazole oxide derivatives as vasodilators. It is also a derivative of Nicorandil (N398500) which is an antiaginal.

Synthesis

The general procedure for the synthesis of N-(2-hydroxyethyl)-3-pyridinecarboxamide from nicotinic acid and 2-aminoethanol was as follows: suspension of nicotinic acid (0.385 g, 3.13 mmol) in anhydrous toluene (15 mL), addition of thionyl chloride (455 μL, 6.26 mmol), and refluxing of the reaction mixture for 4 hours at 140 °C. After cooling, a clarified solution was obtained and the solvent was removed in vacuum. The solid residue was washed three times with ether, followed by the addition of fresh anhydrous toluene (15 mL) and ethanolamine (756 μL, 12.52 mmol). The mixture was stirred at 50 °C overnight. Upon completion of the reaction, the solvent was removed under vacuum and the solid residue was purified by silica gel column chromatography using dichloromethane/methanol (9.2:0.8) as eluent. The final white solid product N-(2-hydroxyethyl)-3-pyridinecarboxamide (450 mg, 86% yield) was obtained with a melting point of 205 °C. The 1H NMR (300 MHz, DMSO-d6) data of the product were as follows: δ 9.00 (s, 1H, NH), 8.68 (m, 2H, Ar-H), 8.17 (d, 1H, Ar-H), 7.60 (m, 1H, Ar-H), 4.74 (m, 1H, OH), 3.51 (m, 2H, CH2), 3.36 (m, 2H CH2).

References

[1] Patent: WO2006/92204, 2006, A1. Location in patent: Page/Page column 16-17
[2] Bioorganic and Medicinal Chemistry, 2016, vol. 24, # 21, p. 5134 - 5147
[3] Archiv der Pharmazie, 2003, vol. 336, # 10, p. 445 - 455

N-(2-HYDROXYETHYL)NITOTINAMIDE(6265-73-2)Related Product Information

• p-Nicorandil
• Nicorandil Impurity 2
• N-[2-(ACETOXY)ETHYL]-3-PYRIDINECARBOXAMIDE
• nicopholine
• N-Nicotinoylglycine
• Nicorandil
• METHYL 2-[[(2-CHLORO-3-PYRIDYL)CARBONYL]AMINO]ACETATE
• METHYL 4-(METHYLTHIO)-2-([[2-(METHYLTHIO)-3-PYRIDYL]CARBONYL]AMINO)BUTANOATE
• N-[2-(METHYLTHIO)NICOTINOYL]-L-LEUCINE
• METHYL 2-([[2-(ETHYLTHIO)-3-PYRIDYL]CARBONYL]AMINO)-4-(METHYLTHIO)BUTANOATE
• (2S)-2-([(2-CHLOROPYRIDIN-3-YL)CARBONYL]AMINO)-4-(METHYLTHIO)BUTANOIC ACID
• DIETHYL 2-([(2-CHLORO-3-PYRIDYL)CARBONYL]AMINO)MALONATE
• MORPHOLINO[6-(1H-PYRAZOL-1-YL)-3-PYRIDINYL]METHANONE
• 3-methyl-2-[(pyridin-3-ylcarbonyl)amino]pentanoic acid
• (2-METHYL-1,6-NAPHTHYRIDIN-3-YL)MORPHOLINOMETHANONE
• ETHYL 2-METHYL-5-OXO-6-(2-([3-(TRIFLUOROMETHYL)BENZOYL]OXY)ETHYL)-5,6-DIHYDRO[1,6]NAPHTHYRIDINE-3-CARBOXYLATE
• ETHYL 6-(2-HYDROXYETHYL)-2-METHYL-5-OXO-5,6-DIHYDRO[1,6]NAPHTHYRIDINE-3-CARBOXYLATE
• N-(PYRIDIN-3-YLCARBONYL)METHIONINE