Pyridine, 3-(4,5-dihydro-2-oxazolyl)- Chemical Properties

Melting point:

71 °C

Boiling point:

260 °C

Density 

1.23±0.1 g/cm3(Predicted)

storage temp. 

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

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly)

form 

Solid

pka

4.13±0.12(Predicted)

color 

Off-White to Pale Yellow

Stability:

Hygroscopic

InChI

InChI=1S/C8H8N2O/c1-2-7(6-9-3-1)8-10-4-5-11-8/h1-3,6H,4-5H2

InChIKey

FVASBRDDSBRETH-UHFFFAOYSA-N

SMILES

C1=NC=CC=C1C1=NCCO1

Pyridine, 3-(4,5-dihydro-2-oxazolyl)- Usage And Synthesis

Uses

2-(3-Pyridyl)-2-oxazoline is an impurity of Nicorandil (N398500). Nicorandil impurity E.

Synthesis

General procedure for the synthesis of 3-(4,5-dihydro-2-oxazolyl)-pyridine from 3-pyridinecarboxaldehyde and 2-aminoethanol: To a solution of 3-pyridinecarboxaldehyde (79 mg, 0.5 mmol), 2-aminoethanol (200 μL, 3.2 mmol), and pyridine (80 μL, 1.0 mmol) in methanol (6 mL) was added PTAB (trimethylphenyltrimethyl ammonium trimethylammonium tribromide, 376 mg, 1.0 mmol). The reaction mixture was stirred at room temperature for 22 hours and then treated with 0.5 M aqueous Na2S2O3 (10 mL) and 1.0 M aqueous NaHCO3 (15 mL), followed by extraction with EtOAc (60 mL). The organic layer was washed sequentially with 0.5 M Na2S2O3 aqueous solution and saturated NaCl aqueous solution and dried with MgSO4. After the solvent was removed under vacuum, the residue was purified by column chromatography on silica gel (Wako C-200), the eluent being a mixture of CCl4 and CCl4-CHCl3 (2:1 v/v) to afford 3-(4,5-dihydro-2-oxazolyl)-pyridine (85 mg) in 86% yield.

References

[1] Heterocycles, 2017, vol. 94, # 5, p. 979 - 990

Pyridine, 3-(4,5-dihydro-2-oxazolyl)-(40055-37-6)Related Product Information

• Nicorandil Impurity 4 Dinitrate
• Nicorandil Impurity 7
• Nicorandil Impurity 6
• Nicorandil Impurity D
• Nicorandil Impurity C
• Nicorandil Impurity 5
• p-Nicorandil
• N-(2-HYDROXYETHYL)NITOTINAMIDE
• ZMZPVNYRPCNJGC-UHFFFAOYSA-N
• 6-Hydroxy Nicorandil
• Nicorandil Impurity 2
• N-[2-(ACETOXY)ETHYL]-3-PYRIDINECARBOXAMIDE
• Nicorandil