6-Quinolinecarboxamide, 4-chloro-7-methoxy-
6-Quinolinecarboxamide, 4-chloro-7-methoxy-
CAS: 417721-36-9
Molecular Formula: C11H9ClN2O2
6-Quinolinecarboxamide, 4-chloro-7-methoxy- - Names and Identifiers
6-Quinolinecarboxamide, 4-chloro-7-methoxy- - Physico-chemical Properties
| Molecular Formula | C11H9ClN2O2 |
| Molar Mass | 236.65 |
| Density | 1.380±0.06 g/cm3(Predicted) |
| Melting Point | >205°C (dec.) |
| Boling Point | 426.7±45.0 °C(Predicted) |
| Solubility | DMSO (Slightly), Methanol (Slightly) |
| Appearance | Solid |
| Color | Off-White to Light Beige |
| pKa | 15.28±0.30(Predicted) |
| Storage Condition | under inert gas (nitrogen or Argon) at 2-8°C |
6-Quinolinecarboxamide, 4-chloro-7-methoxy- - Reference Information
| Application | 4-chloro-7-methoxyquinolin-6-amide is a light yellow solid substance, mainly used as an intermediate of lovatinib. 4-chloro-7-methoxyquinoline-6-amide is a pharmaceutical intermediate that can be used to prepare lenvatinib (E7080). Lovatinib is an oral multi-receptor tyrosine kinase inhibitor developed by Eisai Corporation of Japan. It is a potential treatment for thyroid cancer, liver cancer, non-small cell lung cancer and other solid tumors. |
| Uses | 4-chloro-7-methoxyquinoline-6-amide is an organic synthesis intermediate and a pharmaceutical intermediate, which can be used in laboratory research and development processes and chemical In the production process, it is mainly used as the intermediate of Lovatinib. |
| preparation | step 1, synthesis of 4-cyano -3-methoxyaniline: 134g of 4-cyano -3-hydroxyaniline is taken, dissolved in 500mLN,N-dimethylformamide (DMF) is mixed evenly, 300g of mixture is taken, 32g of tetrabutylammonium bromide and 268g of potassium carbonate are added, the reaction system is heated to 110 ℃, and 100g of dimethyl carbonate is added dropwise, after dropping, the reaction is continued for 8 hours. After the reaction is completed, it is cooled to room temperature, filtered, the filtrate is distilled under reduced pressure to remove the solvent, 200g of water is added, 500mL of ethyl acetate is extracted, anhydrous sodium sulfate in the organic layer is dried, filtered, the filtrate is recovered from the solvent, and the residue is recrystallized with a mixture of petroleum ether and ethyl acetate, in which the volume ratio of petroleum ether to ethyl acetate is 1:1300 to obtain 139g of light yellow solid. Step 2: Synthesis of oxime: 74g of the first step product 4-cyano-3-methoxyaniline is taken, dissolved in ethanol, heated and refluxed, 50g of propionaldehyde acid is added dropwise, and the reaction is continued for 5 hours after the dropwise addition. After the reaction is completed, the solvent is recovered under reduced pressure, and the product continues the next reaction without separation. Step 3, synthesis of 6-cyano-7-methoxy-4-quinolinone: 100mL of polyphosphoric acid is added to the residue of the previous reaction, and the temperature is raised to 90 ℃ for 10h. After the reaction is over, the reaction system is cooled to room temperature, under an ice bath, the reaction solution is poured into ice water, stirred vigorously for 2h, a large amount of white solid is precipitated, filtered, the filter cake is washed to neutral, and vacuum dried to obtain 91g of white solid. Step 4: Synthesis of 6-cyano -7-methoxy -4-chloroquinoline: Take 50g of 6-cyano -7-methoxy -4-quinoline ketone, dissolve it in 80mL of sulfoxide chloride, heat up and refluxing for 5h. After the reaction is completed, the unreacted sulfoxide chloride is recovered under reduced pressure, the residue is poured into ice water, stirred for 1h, filtered, the filter cake is washed to be neutral, and vacuum dried to obtain 52g of white solid powder. Step 5: Synthesis of 4-chloro-7-methoxyquinoline-6-amide: Take 218g of 6-cyano-7-methoxy-4-chloroquinoline and dissolve it in acetic acid solution, wherein the volume ratio of glacial acetic acid to water is 1:1500, and the reaction is heated to 80 ℃ for 24 hours. After the reaction is over, the reaction system is cooled to room temperature, 500mL of ice water is added to the system, stirred overnight, and a large amount of solid is precipitated, filter, filter cake washed to neutral, dry white solid 222g. |
Last Update：2024-04-09 15:16:50
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