4-METHYQUINOLINE-2-CARBOXALDEHYDE synthesis
- Product Name:4-METHYQUINOLINE-2-CARBOXALDEHYDE
- CAS Number:40105-30-4
- Molecular formula:C11H9NO
- Molecular Weight:171.2
Yield:40105-30-4 68%
Reaction Conditions:
with ammonium peroxydisulfate;caesium carbonate in dimethyl sulfoxide at 20; for 24 h;Inert atmosphere;Irradiation;Green chemistry;regioselective reaction;
Steps:
Procedure A for compounds (3a-3p) in Schemes 2
General procedure: Heterocycle (0.10mmol,1equiv)ammonium persulfate (0.30 mmol, 3 equiv), Cs2CO3(0.20mmol,2 equiv)were placed in a dry glass tube.Then, anhydrous DMSO1 mL) and2,2-diethoxyacetic acid (0.7mmol7equiv), wereinjected into the tube by syringe under a N2atmosphere.The solution was then stirred at roomtemperature under the irradiation of 15W blueLEDs strip for 24h.After completion of the reaction,the mixture was quenched by addition of1.2mL of 3.0 M HCl, stirred for 20hthen saturated Na2CO3solution was added to adjust pH tobasicextract with CH2Cl2,the combined organic layers was washed with brine, then dry overanhydrous Na2SO4. The desired products were obtained in thecorresponding yields afterpurification by flashchromatography on silica gel eluting with petroleum and ethylacetate.
References:
Jia, Wei;Jian, Yong;Huang, Binbin;Yang, Chao;Xia, Wujiong [Synlett,2018,vol. 29,# 14,p. 1881 - 1886] Location in patent:supporting information
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