7-BENZYLOXY-4-CHLOROQUINOLINE

Step 3) 7-(benzyloxy)-4-chloroquinolineTo a 100 ml round bottom flask was added 4-chloro-7-hydroxyquinoline (0.89 g, 5 mmol), acetone (40 ml), benzyl bromide(7.5 mmol) and anhydrous K2C03 (2. Og)The reaction was stirred at room temperature, TLC trace detection.After completion of the reaction, acetone was distilled off under reduced pressure, 150 mL of water was added, Extracted with ethyl acetate, the organic phase was combined, acidified with concentrated hydrochloric acid and anhydrous ethanol was added to give a dark oilThe crystals were recrystallized from acetone and the crystals were precipitated and filtered and basified to give a white solid (0.63 g, yield 46.8percent)A 100 ml round bottomed flask was charged with 4-chloro-7-hydroxyquinoline (0.89 g, 5 mmol), acetone (40 ml), benzyl bromide(7.5 mmol) and anhydrous K2CO3 (2.0 g). The reaction was stirred at room temperature and checked by TLC.After completion of the reaction, the acetone was distilled off under reduced pressure, 150 mL of water was added and the mixture was extracted with ethyl acetate. The combined organic phases were acidified with concentrated hydrochloric acid and brought to absolute ethanol with water to give a dark oil. The crystals were recrystallized from acetone to precipitate crystals. To give a white solid (0.63 g, 46.8percent yield).General procedure: A mixture of 4-chloroquinolin-7-ol 8 (0.72g, 4mmol) and anhydrous DMF (10mL) was stirred at room temperature until clear, and then, 60percent NaH (0.4g, 10mmol) and halogenated alkane (20–30mmol) were added. The mixture was stirred at room temperature. After completion of the reaction as indicated by TLC, the solution was poured into HA mixture of 7-substituted 4-chloroquinoline 10a-k (2 mmol), acetone (20 mL), the corresponding aromatic amine (10 mmol) andhydrochloric acid (0.75 mL) was refluxed for 4-8 h. After completion of the reaction as indicated by TLC, the solution waspoured into H2O (100 mL), and extracted with ethyl acetate(50 mL x 3). The combined organic phase was washed with waterand brine and then dried over anhydrous sodium sulfate, filteredand evaporated. The resulting oil was purified by column chromatographyusing a mixture of petroleum ether and ethyl acetate5:1 as the mobile phase to successfully afford the target products11a-x in good yield.A mixture of 7-substituted 4-chloroquinoline 10a-k (2 mmol), acetone (20 mL), the corresponding aromatic amine (10 mmol) andhydrochloric acid (0.75 mL) was refluxed for 4-8 h. After completion of the reaction as indicated by TLC, the solution waspoured into H2O (100 mL), and extracted with ethyl acetate(50 mL x 3). The combined organic phase was washed with waterand brine and then dried over anhydrous sodium sulfate, filteredand evaporated. The resulting oil was purified by column chromatographyusing a mixture of petroleum ether and ethyl acetate5:1 as the mobile phase to successfully afford the target products11a-x in good yield.A mixture of 7-substituted 4-chloroquinoline 10a-k (2 mmol), acetone (20 mL), the corresponding aromatic amine (10 mmol) andhydrochloric acid (0.75 mL) was refluxed for 4-8 h. After completion of the reaction as indicated by TLC, the solution waspoured into H2O (100 mL), and extracted with ethyl acetate(50 mL x 3). The combined organic phase was washed with waterand brine and then dried over anhydrous sodium sulfate, filteredand evaporated. The resulting oil was purified by column chromatographyusing a mixture of petroleum ether and ethyl acetate5:1 as the mobile phase to successfully afford the target products11a-x in good yield.

Molecular Weight:269.72
XLogP3:4.4
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:3
Exact Mass:269.0607417
Monoisotopic Mass:269.0607417
Topological Polar Surface Area:22.1
Heavy Atom Count:19
Complexity:280
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes