| Identification | Back Directory | [Name]
Methyl 4-chloro-7-Methoxyquinoline-6-carboxylate | [CAS]
205448-66-4 | [Synonyms]
lenvaint-D
4-chloro-7-methoxy...
Methyl 4-chloro-7-methoxy...
Methyl 4-chloro-7-Methoxyquinoline-6-carboxylate
4-Chloro-7-methoxyquinoline-6-carboxylic acid methyl ester
4-chloro-7-methoxy-6-Quinolinecarboxylic acid methyl ester
6-Quinolinecarboxylic acid, 4-chloro-7-methoxy-, methyl ester | [EINECS(EC#)]
-0 | [Molecular Formula]
C12H10ClNO3 | [MDL Number]
MFCD17016133 | [MOL File]
205448-66-4.mol | [Molecular Weight]
251.666 |
| Chemical Properties | Back Directory | [Melting point ]
>125oC (dec.) | [Boiling point ]
377.4±37.0 °C(Predicted) | [density ]
1.320±0.06 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,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 |
| Hazard Information | Back Directory | [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. | [Hazard]
Methyl 4-chloro-7-Methoxyquinoline-6-carboxylate may cause an allergic skin reaction and serious eye irritation. | [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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