6-METHOXY-QUINOLINE-2-CARBALDEHYDE synthesis

8synthesis methods

Product Name:6-METHOXY-QUINOLINE-2-CARBALDEHYDE
CAS Number:89060-22-0
Molecular formula:C11H9NO2
Molecular Weight:187.19

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Yield:89060-22-0 91%

Reaction Conditions:

with [bis(acetoxy)iodo]benzene in dimethyl sulfoxide at 120; for 0.5 h;Microwave irradiation;Sealed tube;Green chemistry;regioselective reaction;Solvent;

Steps:

Experimental Procedures Typical experimental procedure for oxidation of 2-methylquinolines

General procedure: Unless otherwise noted, reactions were carried out as following: 2-methylquinolines 1 (2 mmol), PIDA (4 mmol), DMSO(10 mL) were mixed in a sealed microwave tube. The reaction mixture was stirred at 120 °C for 30 min under microwave irradiation using a CEM Discover microwave reactor (the highest power: 85 W; run time: 10 min; hold time: 30 min; temperature: 120 °C). The resulting reaction mixture was neutralized with saturated aqueous NaHCO₃ solution and extracted with Et₂O. The combined organic layers were washed with H₂O and dried over Na₂SO₄, then concentrated under reduced pressure. The crude residue was purified by flash chromatographyon silica gel using hexane/EtOAc as eluent.

References:

Jiang, Long;Huang, Yingyi;Yan, Yiyan;Xie, Yuanyuan [Tetrahedron Letters,2016,vol. 57,# 37,p. 4149 - 4151] Location in patent:supporting information

201230-82-2 Synthesis