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| | 2-METHOXY-3-PYRIDINECARBOXALDEHYDE Basic information |
| | 2-METHOXY-3-PYRIDINECARBOXALDEHYDE Chemical Properties |
| Boiling point | 200-201 °C (lit.) | | density | 1.161 g/mL at 25 °C (lit.) | | refractive index | n20/D 1.5500(lit.) | | Fp | 205 °F | | storage temp. | under inert gas (nitrogen or Argon) at 2–8 °C | | pka | 1.60±0.10(Predicted) | | form | Liquid or Low Melting Solid | | color | Colorless to yellow | | Sensitive | Air Sensitive | | InChI | InChI=1S/C7H7NO2/c1-10-7-6(5-9)3-2-4-8-7/h2-5H,1H3 | | InChIKey | PIFFMIDNNWOQLK-UHFFFAOYSA-N | | SMILES | C1(OC)=NC=CC=C1C=O | | CAS DataBase Reference | 71255-09-9(CAS DataBase Reference) |
| Hazard Codes | Xi | | Risk Statements | 41-43-36/37/38 | | Safety Statements | 26-36/37/39-37 | | WGK Germany | 3 | | HazardClass | IRRITANT | | HS Code | 29339900 | | Storage Class | 10 - Combustible liquids | | Hazard Classifications | Eye Dam. 1
Skin Sens. 1 |
| | 2-METHOXY-3-PYRIDINECARBOXALDEHYDE Usage And Synthesis |
| Chemical Properties | Colorless to yellow liquid | | Uses | 2-Methoxy-3-pyridinecarboxaldehyde may be used to synthesize the following:
- ethyl 5-amino-4-(2-methoxy-3-pyridyl)-2-methyl-6,7,8,9-tetrahydro-4H-pyrano[2,3-b]quinoline-3-carboxylate, a potent AChE inhibitor
- N-hydroxy-2-pyridinone-based arylsulfone containing a Zn-binding group (ZBG) as MMP-2/-9 inhibitor
| | Synthesis Reference(s) | Tetrahedron Letters, 29, p. 773, 1988 DOI: 10.1016/S0040-4039(00)80206-3 | | Synthesis | Sodium metal (0.35 g, 15.0 mmol) was slowly added to dry methanol (6 mL) at 0 °C and stirred until completely dissolved. Subsequently, a solution of anhydrous methanol (2 mL) of 2-chloro-3-pyridinecarboxaldehyde (0.708 g, 5.0 mmol) was added to the reaction system via syringe. The reaction mixture was heated to reflux temperature and maintained for 5 hours. Upon completion of the reaction, the mixture was cooled to room temperature and the solvent was subsequently evaporated under reduced pressure. The residue was dissolved in water (10 mL), neutralized with dilute hydrochloric acid and extracted with ether (3 x 10 mL). The organic phases were combined, dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by fast column chromatography (eluent: petroleum ether/ethyl acetate, 4:1) to afford the target compound 2-methoxy-3-pyridine aldehyde (0.473 g, 69% yield) as a colorless oil.1H NMR (300 MHz, CDCl3) δ 10.34 (d, J = 0.8 Hz, 1H), 8.36 (dd, J = 4.9, 2.1 Hz, 1H), 8.09 (dd, J = 7.4, 2.1 Hz, 1H), 7.00 (ddd, J = 7.4, 4.9, 0.8 Hz, 1H), 4.07 (s, 3H). 13C NMR (75 MHz, CDCl3) δ 189.1, 164.4, 152.8, 137.6, 118.8, 117.3, 54.0. | | References | [1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 14, p. 3933 - 3937
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1990, # 9, p. 2409 - 2415 |
| | 2-METHOXY-3-PYRIDINECARBOXALDEHYDE Preparation Products And Raw materials |
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