4-Chloro-7-methoxyquinoline Chemical Properties

Melting point:

75-77

Boiling point:

299.9±20.0 °C(Predicted)

Density 

1.267±0.06 g/cm3(Predicted)

storage temp. 

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

pka

3.89±0.27(Predicted)

form 

solid

color 

Off-white to light yellow

InChI

InChI=1S/C10H8ClNO/c1-13-7-2-3-8-9(11)4-5-12-10(8)6-7/h2-6H,1H3

InChIKey

UKTYNFPTZDSBLR-UHFFFAOYSA-N

SMILES

N1C2C(=CC=C(OC)C=2)C(Cl)=CC=1

CAS DataBase Reference

68500-37-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

22-41

Safety Statements 

26-39

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

2933491090

4-Chloro-7-methoxyquinoline Usage And Synthesis

Application

4-Chloro-7-methoxyquinoline is an important intermediate for anticancer drugs and has wide applications in the synthesis of pharmaceuticals, dyes, pesticides and chemical auxiliaries; its products have good therapeutic effects in antimalarial, bactericidal, anti-inflammatory and antitumor effects.

Chemical Properties

yellow powder

Synthesis

1. 3-Methoxyaniline (1.23 g) and 5-methoxymethylene-2,2-dimethyl-[1,3]dioxane-4,6-dione (1.90 g) were dissolved in 2-propanol (40 ml), and the reaction was stirred at 70 °C for 1 hour. After completion of the reaction, the solvent was removed by distillation under reduced pressure and the residue was washed with ether to afford 5-[(3-methoxyphenylamino)-methylene]-2,2-dimethyl-[1,3]dioxane-4,6-dione (1.22 g, 44% yield). 2. 5-[(3-methoxyphenylamino)-methylene]-2,2-dimethyl-[1,3]dioxane-4,6-dione (1.22 g) was suspended in diphenyl ether (15 ml) with biphenyl (5.1 g) and reacted with stirring at 220 °C for 1.5 hrs. The reaction mixture was purified by column chromatography in methanol-chloroform system to afford 7-methoxy-1H-quinolin-4-one (394 mg, 51% yield). 3. 7-Methoxy-1H-quinolin-4-one (394 mg) was suspended in diisopropylethylamine (3 ml), phosphorus trichloride (1 ml) was added, and the reaction was stirred at 100 °C for 1 hour. After completion of the reaction, water was added under cooling in an ice bath, the aqueous layer was neutralized with aqueous sodium bicarbonate and the organic layer was extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried with anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure and the residue was purified by column chromatography in acetone-chloroform system to afford 4-chloro-7-methoxyquinoline (312 mg, 72% yield).

References

[1] Patent: EP1724268, 2006, A1. Location in patent: Page/Page column 46
[2] European Journal of Medicinal Chemistry, 2013, vol. 63, p. 907 - 923

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