6-Hydroxy-2(1H)-3,4-dihydroquinolinone CAS 54197-66-9
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) |
Safety Information
| 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 |
| 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 | 19313-87-2 54197-66-9 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
| Raw materials | 2-Propenoic acid, 3-(5-hydroxy-2-nitrophenyl)--->3-CHLORO-N-(4-METHOXYPHENYL)PROPANAMIDE-->3-CHLORO-N-PHENYLPROPANAMIDE-->1,2,3,4-Tetrahydroquinoline-->6-AMINO-3,4-DIHYDRO-1H-QUINOLIN-2-ONE-->3-CHLORO-N-(4-ETHOXYPHENYL)PROPANAMIDE-->3-CHLORO-N-(4-HYDROXYPHENYL)PROPIONAMIDE-->3,4-DIHYDROQUINOLIN-2(1H)-ONE-->Aluminum chloride-->p-Anisidine |
| Preparation Products | Disperse Yellow HG-->Nedocromil-->Cilostazol Related Compound C (50 mg) (1-(4-(5-Cyclohexyl-1H-tetrazol-1-yl)butyl)-6-(4-(1-cyclohexyl-1H-tetrazol-5-yl)butoxy)-3,4-dihydroquinolin-2(1H)-one) |
