Methyl 7-Methoxy-4-oxo-1,4-dihydroquinoline-6-carboxylate

Product NameMethyl 7-Methoxy-4-oxo-1,4-dihydroquinoline-6-carboxylate
CAS205448-65-3
MFC12H11NO4
MW233.22
EINECS000-000-0
MOL File205448-65-3.mol

Chemical Properties

Boiling point	421.0±45.0 °C(Predicted)
Density	1.267±0.06 g/cm3(Predicted)
storage temp.	2-8°C, protect from light
pka	-0.53±0.50(Predicted)
Appearance	Off-white to light yellow Solid
InChI	InChI=1S/C12H11NO4/c1-16-11-6-9-7(10(14)3-4-13-9)5-8(11)12(15)17-2/h3-6H,1-2H3,(H,13,14)
InChIKey	TYKSVPGCVLNVIO-UHFFFAOYSA-N
SMILES	N1C2=C(C=C(C(OC)=O)C(OC)=C2)C(=O)C=C1

Safety Information

HS Code

2933499090

Usage And Synthesis

Uses

Methyl 7-methoxy-4-oxo-1,4-dihydroquinoline-6-carboxylate serves as a precursor for chloroquinoline intermediates: treatment with thionyl chloride and a catalytic amount of DMF at 125 °C converts it to the corresponding 4-chloroquinoline[6].

Synthesis

4-[(2,2-Dimethyl-4,6-dioxo-[1,3]dioxan-5-ylidenemethyl)-amino]-2-methoxy-benzoic acid methyl ester

205448-64-2

205448-65-3

General procedure for the synthesis of methyl 7-methoxy-4-oxo-1,4-dihydroquinoline-6-carboxylate from methyl 4-((2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-yl)methylamino)-2-methoxybenzoate: 5-((3-methoxy-4-methoxycarbonyloxyanilino)methylene-2,2-dimethyl-1,3-dioxane-4, 6-dione (10 g, 29.8 mmol) was suspended in DOWTHERM A (125 ml) and heated to 180-190 °C within 30 min. The raw material dissolved at 100°C and carbon dioxide began to be released at about 180°C. Heating was continued for 30 minutes and then stopped. As the reaction mixture cooled, the product gradually precipitated. When the temperature drops to 40°C, ether is added and the mixture is stirred for 30 minutes. The solid product was collected by filtration, washed with ether and dried under vacuum to afford 7-methoxy-6-methoxycarbonyl-1,4-dihydroquinolin-4-one (5.56 g, 80% yield). The structure of the product was confirmed by 1H NMR spectroscopy: (DMSO-d6) δ 3.80 (s, 3H); 3.85 (s, 3H); 5.95 (d, 1H); 7.00 (s, 1H); 7.85 (d, 1H); 8.40 (s, 1H); 11.6 (br s, 1H); MS-ESI: 234 [MH]+.

References

[1] Patent: US6809097, 2004, B1. Location in patent: Page column 67
[2] Journal of Medicinal Chemistry, 2008, vol. 51, # 6, p. 1649 - 1667
[3] Journal of Medicinal Chemistry, 2008, vol. 51, # 6, p. 1668 - 1680
[4] Patent: EP1724268, 2006, A1. Location in patent: Page/Page column 48
[5] Patent: EP3293177, 2018, A1. Location in patent: Paragraph 0199; 0201
[6] Weiss, M. M., Harmange, J.-C., Polverino, A. J., Bauer, D., Berry, L., Berry, V., Borg, G., Bready, J., Chen, D., Choquette, D., Coxon, A., DeMelfi, T., Doerr, N., Estrada, J., Flynn, J., Graceffa, R. F., Harriman, S. P., Kaufman, S., La, D. S., … Zanon, R. (2008). Evaluation of a Series of Naphthamides as Potent, Orally Active Vascular Endothelial Growth Factor Receptor-2 Tyrosine Kinase Inhibitors. Journal of Medicinal Chemistry, 51(6), 1668–1680. https://doi.org/10.1021/jm701098w

Methyl 7-Methoxy-4-oxo-1,4-dihydroquinoline-6-carboxylate

Chemical Properties

Safety Information

Usage And Synthesis

Preparation Products And Raw materials

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