Methyl 6-quinolinecarboxylate

White solid

6.0 mmol of thionyl chloride was slowly added to 2.0 mmol of 6-quinolinecarboxylic acid dissolved in 5 mL of methanol at 0 and the reaction mixture was stirred at 50 for 12 hours. 30 mL of saturated aqueous NaHCOQuinoline-6-carboxylic acid (510 mg, 2.95 mmol, 1.0 eq.)Dissolved in 20 ml of methanol, Add 1 ml concentrated sulfuric acid, The reaction was stirred overnight at 50 °C.Cool to room temperature, add saturated aqueous sodium bicarbonate, with ethyl acetateExtraction, liquid separation, drying of the organic phase over anhydrous sodium sulfate, filtration, and concentration under reduced pressure gave the methyl ester of quinolin-6-carboxylic acid as a white solid (540 mg, yield: 89percent).Step 2:To a solution of quinoline-6- carboxylic acid (183 g, 1.06 mol) in methanol (1 lit.), thionyl chloride (150.7 g, 1.2 mol) was added dropwise at 0°C and then stirred at 65°C for 12h. The reaction mixture was concentrated and to the residue dichloromethane and aqueous sodium carbonate solutions were added. The organic layer was dried with sodium sulphate and concentrated to afford the title compound as a brown solid (150 g, 75percent).Step 2: Methyl quinoline-6-carboxylate: To a solution of quinoline-6-carboxylic acid (183 g, 1.06 mol) in methanol (1 lit.), thionyl chloride (150.7 g, 1.2 mol) was added drop wise at 0°C and then stirred at 65°C for 12h. The reaction mixture was concentrated and to the residue dichloromethane and aqueous sodium carbonate solutions were added. The organic layer was dried with sodium sulphate and concentrated to afford the title compound as a brown solid (150 g, 75percent).Step 2: General procedure: To a 25-mL Schlenk tube equipped with a magnetic stirrer, PdClGeneral procedure: To a 10 mL round bottom flask equipped with a magnetic stir bar, 1, 2, 3, 4-tetrahydroquinoline (0.5 mmol), DEAD solution 40 wtpercent in toluene (2.2 eq, 1.1 mmol, 0.5 mL), and CHCl

Molecular Weight:187.19
XLogP3:2.3
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:187.063328530
Monoisotopic Mass:187.063328530
Topological Polar Surface Area:39.2
Heavy Atom Count:14
Complexity:217
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes