2-CHLORO-6-METHOXY-QUINOLINE Chemical Properties

Melting point:

106-107℃

Boiling point:

310.5±22.0 °C(Predicted)

Density 

1.267

storage temp. 

Inert atmosphere,Room Temperature

pka

0.37±0.43(Predicted)

form 

solid

Appearance

White to yellow Solid

Safety Information

Hazard Codes 

Xn

Risk Statements 

22-41

Safety Statements 

26-39

WGK Germany 

3

HS Code 

2933499090

2-CHLORO-6-METHOXY-QUINOLINE Usage And Synthesis

Synthesis

General procedure for the synthesis of 2-chloro-6-methoxyquinoline from 6-methoxyquinolin-2(1H)-one: 6-methoxyquinolin-2-ol (400 mg, 2.29 mmol) was dissolved in phosphorus trichloride (5.0 mL) and the reaction was carried out at reflux for 2 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure. The residue was dissolved in ethyl acetate (50 mL) and the organic layer was washed sequentially with saturated sodium bicarbonate solution (30 mL × 2). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated to give the crude product. The crude product was purified by silica gel column chromatography (petroleum ether/ethyl acetate = 10:1) to afford 2-chloro-6-methoxyquinoline (380 mg, 86% yield) as a white solid.1H NMR (CDCl3, 400 MHz): δ 7.92 (d, J = 8.4 Hz, 1H), 7.85 (d, J = 9.2 Hz, 1H), 7.32-7.25 ( m, 2H), 7.00 (d, J = 2.4 Hz, 1H), 3.86 (s, 3H).

References

[1] Patent: WO2012/48181, 2012, A1. Location in patent: Page/Page column 74
[2] Patent: WO2012/83165, 2012, A1. Location in patent: Page/Page column 91
[3] Ann. Inst. Pasteur, 1930, vol. 44, p. 719,736

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