Methyl 4-chloro-7-Methoxyquinoline-6-carboxylate Chemical Properties

Melting point:

>125oC (dec.)

Boiling point:

377.4±37.0 °C(Predicted)

Density 

1.320±0.06 g/cm3(Predicted)

storage temp. 

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

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

2.98±0.30(Predicted)

color 

Light Orange to Orange

InChI

InChI=1S/C12H10ClNO3/c1-16-11-6-10-7(9(13)3-4-14-10)5-8(11)12(15)17-2/h3-6H,1-2H3

InChIKey

DDDSGYZATMCUDW-UHFFFAOYSA-N

SMILES

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

Safety Information

HS Code 

2933499090

Methyl 4-chloro-7-Methoxyquinoline-6-carboxylate Usage And Synthesis

Chemical Properties

4-Chloro-7-methoxyquinoline-6-carboxylic acid methyl ester is bright yellow or orange solid at room temperature and normal pressure, it belongs to benzene quinoline derivatives, with a certain degree of alkalinity, it is mainly used in the synthesis of drugs, dyes.

Uses

Methyl-4-Chloro-7-methoxyquinoline-6-carboxylate is used pharmaceutically for treating infection after burns. It is also used as reagents in the preparation of naphthamides as inhibitors of vascular endothelial growth factor (VEGF) receptor tyrosine kinase.

Synthesis

Methyl 7-methoxy-4-oxo-1,4-dihydroquinoline-6-carboxylate (3.00 g, 12.86 mmol) was added to thionyl chloride (30.00 mL). N,N-dimethylformamide (93.99 mg, 1.29 mmol) was then added to the reaction system. The reaction solution was heated to an external temperature of 90 °C under nitrogen protection and reacted under reflux conditions for 1 hour. The reaction process was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the aqueous phase was combined and concentrated to dryness. The residue was dissolved in ice water (50 mL) and extracted with ethyl acetate (20 mL x 2). The aqueous phase was then extracted with dichloromethane (30 mL x 5). The dichloromethane phases were combined, washed with sodium chloride solution (20 mL × 2), dried over anhydrous sodium sulfate, and subsequently concentrated under reduced pressure by pumping to afford methyl 4-chloro-7-methoxyquinoline-6-carboxylate (2.60 g, 9.81 mmol) in 76.32% yield and 95% purity as a mixed solid. The product was characterized by 1H NMR (400 MHz, DMSO-d6): δ 3.87 (s, 3H), 3.98 (s, 3H), 7.60 (s, 1H), 7.66 (d, J = 4.77 Hz, 1H), 8.41 (s, 1H), 8.83 (d, J = 4.77 Hz, 1H).

References

[1] Journal of Medicinal Chemistry, 2008, vol. 51, # 6, p. 1649 - 1667
[2] Patent: EP3293177, 2018, A1. Location in patent: Paragraph 0251; 0252
[3] Patent: US6809097, 2004, B1. Location in patent: Page column 67
[4] Journal of Medicinal Chemistry, 2008, vol. 51, # 6, p. 1668 - 1680
[5] Patent: EP1724268, 2006, A1. Location in patent: Page/Page column 48

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