4-Chloro-7-hydroxyquinoline Chemical Properties

Boiling point:

329.3±22.0 °C(Predicted)

Density 

1.412±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

8.41±0.40(Predicted)

Appearance

Off-white to light yellow Solid

Safety Information

HS Code 

2933499090

4-Chloro-7-hydroxyquinoline Usage And Synthesis

Uses

4-Chloro-7-hydroxyquinoline is a reagent used in the synthesis of novel benzo[d]?oxazol-?2(3H)?-?one derivatives which can act as c-Met kinase inhibitors.

Synthesis

General procedure for the synthesis of 4-chloro-7-hydroxyquinoline using 4-chloro-7-methoxyquinoline as starting material: 4-chloro-7-methoxyquinoline (3.86 g, 20 mmol), 40% hydrobromic acid (30 mL) and acetic anhydride (20 mL) were mixed and heated to reflux, and the progress of the reaction was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the reaction mixture was cooled to room temperature. Subsequently, 100 mL of water was added to the reaction mixture and the pH was adjusted to 6.0 with 20% sodium hydroxide solution, at which point a large amount of solid precipitated. After filtration, washing and drying, an off-white solid product (3.53 g, 98.6% yield) was obtained.

References

[1] Patent: CN105037266, 2017, B. Location in patent: Paragraph 0323-0326
[2] Patent: CN105017145, 2017, B. Location in patent: Paragraph 0327; 0328; 0329
[3] Patent: CN106749231, 2017, A. Location in patent: Paragraph 0116; 0117; 0118; 0119
[4] European Journal of Medicinal Chemistry, 2019, p. 666 - 678

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