2-Chloro-3-formyl-6-methylquinoline

2) 3.5 ml of DMF and 17 ml of POCl3 were mixed under ice-cooling, After stirring, 2.24 g (15 mmol) of compound 1 was added, and the resulting solution was placed in a reflux apparatus, Heated to 90 ° C for 10 hours, cooled and poured into 500 ml of ice water, and the compound 2(2.7 g, yield 87percent).2) 3.5 ml DMF and 17 ml POClThis example provides a process for the synthesis of 2-chloro-3-formyl-6-methylquinoline with the following main steps: under ice-salt bath, 3.00g (20.13 mmol) acetanilide, 8.03 g (27.04 mmol) of BTC and 10 mL of trichloromethane 4.2 mL (54.66mmol) DMF was added dropwise over 80 min after the temperature was maintained below -5 °C. The rate of the bubble overflow was controlled by the tail gas uptake rate. After the addition of the DMF, the mixture was stirred continuously for 10 min. For water bath, plus Heat to 51 °C, reaction 5 hours, steaming part of the solvent, adding ice water, 10percent NaOH to adjust the pH to 8 ~ 9, pumping, recrystallization. The yield was 84.83percent.General procedure: At 0 °C to a stirred solution of POCl3 (39.6 g, 259 mmol) and anhydrous DMF (8 g, 111mmol) was added acetanilide (5 g, 37 mmol). The mixture was then heated to 65 °C and the progress of the reaction was monitored by TLC analysis. After 8 h the reaction mixturewas then cooled to room temperature and added cautiously into ice-cold water. The solid precipitated was collected by filtration to isolate the compound 1a as yellow solid.POClGeneral procedure: Dimethylformamide (12 mmol, 3 equiv.) was cooled at 0°C in a round flask equipped with a drying tube and phosphorus pentachloride (18 mmol, 4.5 equiv.) was added slowly and the mixture was stirred for 15 minutes keeping the temperature below 0°C. To this solution was added in a portion the corresponding acetanilide (4 mmol, 1 equiv.) and the reaction mixture was heated under reflux and stirring for the appropiate time depending of the acetanilide. The resulted mixture was cooled to 0°C and the solution was poured slowly into ice-water and stirring for ten minutes, obtaining a yellow solid which was filtered, washed several time with cold water and dried under vacuum. The 2-chloroquinoline-3-carbaldehydes were recrystallized according to the literature.Step 2: General procedure: To the prepared TCTA–DMFreagent, 9.8 mmol of the Acetanilide was added and stirred under refluxconditions. Progress of the reaction was checked by TLC till the completion ofthe reaction. Analytical TLC was carried out using Merck aluminum-backed0.2 mm silica gel 60 F-254 plates. Column chromatography was conductedusing Merck silica gel 60 (230–400 mesh). After completion of the reaction, water was added to the reaction mixture and stirred for a few more minutes toextract inorganic components into water. The organic layer was separated andthe crude product thus obtained was further purified with columnchromatography (silica gel, ethyl acetate/n-hexane)

Molecular Weight:205.64
XLogP3:3
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:205.0294416
Monoisotopic Mass:205.0294416
Topological Polar Surface Area:30
Heavy Atom Count:14
Complexity:221
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes