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| | 4-Chloro-7-methoxyquinoline Basic information | | Application |
| Product Name: | 4-Chloro-7-methoxyquinoline | | Synonyms: | 4-CHLORO-7-METHOXYQUINOLINE;7-Methoxy-4-chloroquinoline;4-Chloro-7-methoxy-1-azanaphthalene;Quinoline, 4-chloro-7-methoxy-;4-Cholro-7-Methoxyquinoline;4-Chloro-7-methoxyquinoline, >=97%;4-Chloro-7-methoxyquinoline ISO 9001：2015 REACH | | CAS: | 68500-37-8 | | MF: | C10H8ClNO | | MW: | 193.63 | | EINECS: | 676-017-8 | | Product Categories: | | | Mol File: | 68500-37-8.mol |  |
| | 4-Chloro-7-methoxyquinoline Chemical Properties |
| Melting point | 75-77 | | Boiling point | 299.9±20.0 °C(Predicted) | | density | 1.267±0.06 g/cm3(Predicted) | | storage temp. | under inert gas (nitrogen or Argon) at 2-8°C | | pka | 3.89±0.27(Predicted) | | form | solid | | color | Off-white to light yellow | | InChI | InChI=1S/C10H8ClNO/c1-13-7-2-3-8-9(11)4-5-12-10(8)6-7/h2-6H,1H3 | | InChIKey | UKTYNFPTZDSBLR-UHFFFAOYSA-N | | SMILES | N1C2C(=CC=C(OC)C=2)C(Cl)=CC=1 | | CAS DataBase Reference | 68500-37-8(CAS DataBase Reference) |
| Hazard Codes | Xi,Xn | | Risk Statements | 22-41 | | Safety Statements | 26-39 | | WGK Germany | 3 | | Hazard Note | Irritant | | HS Code | 2933491090 |
| | 4-Chloro-7-methoxyquinoline Usage And Synthesis |
| Application | 4-Chloro-7-methoxyquinoline is an important intermediate for anticancer drugs and has wide applications in the synthesis of pharmaceuticals, dyes, pesticides and chemical auxiliaries; its products have good therapeutic effects in antimalarial, bactericidal, anti-inflammatory and antitumor effects. | | Chemical Properties | yellow powder | | Synthesis | 1. 3-Methoxyaniline (1.23 g) and 5-methoxymethylene-2,2-dimethyl-[1,3]dioxane-4,6-dione (1.90 g) were dissolved in 2-propanol (40 ml), and the reaction was stirred at 70 °C for 1 hour. After completion of the reaction, the solvent was removed by distillation under reduced pressure and the residue was washed with ether to afford 5-[(3-methoxyphenylamino)-methylene]-2,2-dimethyl-[1,3]dioxane-4,6-dione (1.22 g, 44% yield).
2. 5-[(3-methoxyphenylamino)-methylene]-2,2-dimethyl-[1,3]dioxane-4,6-dione (1.22 g) was suspended in diphenyl ether (15 ml) with biphenyl (5.1 g) and reacted with stirring at 220 °C for 1.5 hrs. The reaction mixture was purified by column chromatography in methanol-chloroform system to afford 7-methoxy-1H-quinolin-4-one (394 mg, 51% yield).
3. 7-Methoxy-1H-quinolin-4-one (394 mg) was suspended in diisopropylethylamine (3 ml), phosphorus trichloride (1 ml) was added, and the reaction was stirred at 100 °C for 1 hour. After completion of the reaction, water was added under cooling in an ice bath, the aqueous layer was neutralized with aqueous sodium bicarbonate and the organic layer was extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried with anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure and the residue was purified by column chromatography in acetone-chloroform system to afford 4-chloro-7-methoxyquinoline (312 mg, 72% yield). | | References | [1] Patent: EP1724268, 2006, A1. Location in patent: Page/Page column 46
[2] European Journal of Medicinal Chemistry, 2013, vol. 63, p. 907 - 923 |
| | 4-Chloro-7-methoxyquinoline Preparation Products And Raw materials |
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