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| | 6-Hydroxy-2(1H)-3,4-dihydroquinolinone Basic information |
| Product Name: | 6-Hydroxy-2(1H)-3,4-dihydroquinolinone | | Synonyms: | 6-HYDROXY-1,2,3,4-TETRAHYDRO-2-QUINOLINONE;6-HYDROXY-2(1H)-3,4-DIHYDROQUINOLINONE;6-HQ;6-HYDROXYL-3,4-DIHYDROCARBOSTYRIL;6-HYDROXY-3,4-DIHYDRO-1H-QUINOLIN-2-ONE;TQ(3,4-Dihydro-6-Hydroxy-2(1H)CQuinolinone);TQ(3,4-DIHYDRO-6-HYDROXY-2(1H)QUINOLINONE);Hydroxyl-3,4-dihydrocarbostyril | | CAS: | 54197-66-9 | | MF: | C9H9NO2 | | MW: | 163.17 | | EINECS: | 611-111-4 | | Product Categories: | Fluorobenzene;Alcohols and Derivatives;Heterocycles;Aromatic Ethers;Quinoline derivatives;API intermediates;(intermediate of cilostazol);Various Metabolites and Impurities;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;john's | | Mol File: | 54197-66-9.mol |  |
| | 6-Hydroxy-2(1H)-3,4-dihydroquinolinone Chemical Properties |
| Melting point | 236-240 °C | | Boiling point | 424.5±45.0 °C(Predicted) | | density | 1.282±0.06 g/cm3(Predicted) | | storage temp. | Sealed in dry,Room Temperature | | solubility | DMSO (Slightly), Methanol (Slightly, Heated) | | form | solid | | pka | 9.86±0.20(Predicted) | | color | White to Almost white | | InChI | InChI=1S/C9H9NO2/c11-7-2-3-8-6(5-7)1-4-9(12)10-8/h2-3,5,11H,1,4H2,(H,10,12) | | InChIKey | HOSGXJWQVBHGLT-UHFFFAOYSA-N | | SMILES | N1C2=C(C=C(O)C=C2)CCC1=O | | CAS DataBase Reference | 54197-66-9(CAS DataBase Reference) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26 | | WGK Germany | 3 | | Hazard Note | Irritant | | HS Code | 2933790002 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | 6-Hydroxy-2(1H)-3,4-dihydroquinolinone Usage And Synthesis |
| Chemical Properties | 6-Hydroxy-2(1H)-3,4-dihydroquinolinone Appearance is white to almost white powder to crystal, Melting point 238°C, Store at -20° C. | | Uses | A metabolite of Cilostazole. | | Synthesis | 2) 98 g of 3-chloro-N-(4-methoxyphenyl)acrylamide obtained from step 1) was mixed with N-(4-methoxyphenyl)-3-chloroacrylamide, 500 mL of tetrahydrofuran and 98 g of palladium chloride. The reaction mixture was heated to 100 °C under 5 MPa pressure and maintained at that temperature. Upon completion of the reaction, it was cooled to room temperature and then maintained at 110°C for 3 hours. Subsequently, filtration was performed and the filtrate was rotary evaporated to dryness to obtain 6-hydroxy-3,4-dihydro-2(1H)-quinolone crude.3) The 6-hydroxy-3,4-dihydro-2(1H)-quinolone crude obtained in step 2) was dissolved in 50 mL of ethanol, recrystallized and decolorized using activated carbon. After filtration, 74 g of 6-hydroxy-3,4-dihydro-2(1H)-quinolinone was obtained as an off-white solid in 95% yield. The total yield was 85%. | | References | [1] Patent: CN108383781, 2018, A. Location in patent: Paragraph 0033; 0034
[2] Patent: CN107325078, 2017, A. Location in patent: Paragraph 0039-0040; 0043-0044; 0046-0047; 0049-0050; 0052
[3] Journal of the Chinese Chemical Society, 2000, vol. 47, # 1, p. 155 - 162
[4] Heterocycles, 2009, vol. 78, # 1, p. 189 - 195
[5] Asian Journal of Chemistry, 2011, vol. 23, # 4, p. 1655 - 1660 |
| | 6-Hydroxy-2(1H)-3,4-dihydroquinolinone Preparation Products And Raw materials |
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