|
|
| | Methyl 7-Methoxy-4-oxo-1,4-dihydroquinoline-6-carboxylate Basic information |
| Product Name: | Methyl 7-Methoxy-4-oxo-1,4-dihydroquinoline-6-carboxylate | | Synonyms: | Methyl 7-Methoxy-4-oxo-1,4-dihydroquinoline-6-carboxylate;1,4-Dihydro-7-methoxy-4-oxo-6-quinolinecarboxylic acid methyl ester;7-Methoxy-4-oxo-1,4-dihydro-quinoline-6-carboxylic acid methyl ester;Lenvatinib Intermediate3;FMX14227-A2;7-Methoxy-4-oxo-1,4-dihydroquinoline-6-carboxylate;methyl 4-hydroxy-7-methoxyquinoline-6-carboxylate;Methyl 7-Methoxy-4-oxo-1 | | CAS: | 205448-65-3 | | MF: | C12H11NO4 | | MW: | 233.22 | | EINECS: | 000-000-0 | | Product Categories: | | | Mol File: | 205448-65-3.mol |  |
| | 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 |
| | 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 |
| | Methyl 7-Methoxy-4-oxo-1,4-dihydroquinoline-6-carboxylate Preparation Products And Raw materials |
|