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

Methyl 7-Methoxy-4-oxo-1,4-dihydroquinoline-6-carboxylate Usage And Synthesis

Synthesis

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

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